1h-pyrrolo[2,3-b]pyridines and preparation and uses thereof

ABSTRACT

Pyrrolo[2,3-b]pyridine compound for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of pyrrolo[2,3-b]pyridine compound or analogs thereof, in the treatment of disorders characterized by overexpression of DYRK1A (e.g., cancer, Down syndrome, Alzheimer&#39;s disease, diabetes, viral infections, and osteoarthritis).

RELATED APPLICATIONS

This application claims the benefit of U.S. Provisional Application No.63/254,713, filed Oct. 12, 2021, which is incorporated herein byreference in its entirety.

BACKGROUND Technical Field

This disclosure relates to inhibitors of dual-specificity tyrosinephosphorylation-regulated 1A kinase, and compositions comprising thesame. More particularly, it concerns the use of a pyrrolo[2,3-b]pyridinecompound or salts or analogs thereof, in the treatment of disorderscharacterized by the abnormal expression and/or activity of DYRK1A(e.g., cancer, Down syndrome, Alzheimer's disease, diabetes, viralinfections, and osteoarthritis).

Background

Dual-specificity tyrosine phosphorylation-regulated kinases (DYRK1A, 1B,2-4) comprise a family of protein kinases within the CMGC group of theeukaryotic kinome. These protein kinases are involved in multiplecellular functions, including intracellular signaling, mRNA splicing,chromatin transcription, DNA damage repair, cell survival, cell cyclecontrol, differentiation, homocysteine/methionine/folate regulation,body temperature regulation, endocytosis, neuronal development, synapticplasticity, etc. Abnormal expression and/or activity of some of thesekinases, DYRK1A in particular, is seen in many human nervous systemdiseases, such as cognitive deficits associated with Down syndrome,Alzheimer's disease, and related diseases, tauopathies, dementia, Pick'sdisease, Parkinson's disease, and other neurodegenerative diseases,Phelan-McDermid syndrome, autism, and CDKL5 deficiency disorder. DYRKsare also involved in diabetes, abnormal folate/methionine metabolism,osteoarthritis, several solid cancers (glioblastoma, breast, andpancreatic cancers) and leukemias (acute lymphoblastic leukemia, acutemegakaryoblastic leukemia), viral infections (influenza, HIV-1, HCMV,HCV, CMV, HPV), as well as infections caused by unicellular parasites(Leishmania, Trypanosoma, Plasmodium) (International Journal ofMolecular Sciences (2021), 22(11), 6047). DYRK1A has also beenidentified as a critical stabilizer of EGFR (Cell Death & Disease(2019), 10, 282) which is a crucial factor contributing to thekeratinization, cell hyperproliferation, abnormal differentiation andinflammatory infiltration during the progress of psoriasis.

SUMMARY

The present disclosure provides methods and reagents, involvingcontacting a cell with an agent, such as an pyrrolo[2,3-b]pyridinecompound, in a sufficient amount to antagonize DYRK1A activity, e.g.,reduced the proliferation of head and neck squamous cell carcinoma,luminal/HER2 breast cancer (Cell (2016), 164(1-2), 293-309) orpancreatic adenocarcinoma, as well as impaired the self-renewal capacityof glioblastoma and compromised ovarian cancer spheroid cell viability(Molecular Cancer Research (2017), 15(4), 371-381).

The present disclosure also provides methods and reagents, involvingcontacting a cell with an agent, such as a pyrrolo[2,3-b]pyridinecompound, in a sufficient amount to antagonize DYRK1A activity, e.g., i)to normalize prenatal and early postnatal brain development; ii) toimprove cognitive function in youth and adulthood; and/or iii) toattenuate Alzheimer's-type neurodegeneration.

Some embodiments disclosed herein include DYRK1A inhibitors containing apyrrolo[2,3-b]pyridine core. Other embodiments disclosed herein includepharmaceutical compositions and methods of treatment using thesecompounds.

One embodiment disclosed herein includes a compound having the structureof Formula I:

or a pharmaceutically acceptable salt thereof,

wherein:

R¹ is selected from the group consisting of 6-membered heteroaryloptionally substituted with 1-4 R⁵ and 7-14-membered heteroaryloptionally substituted with 1-10 R⁶;

wherein a carbon atom on an aromatic ring of the heteroaryl R¹ groupforms the bond with

R² is selected from the group consisting of H, —OR⁷, and 5-memberedheteroaryl optionally substituted with 1-3 R⁸, and —NHR⁹;

R³ is selected from the group consisting of H, halide, CN, —CO₂H, —OR¹⁰,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R¹¹, -(5-9membered heteroaryl) optionally substituted with 1-10 R¹²; phenyloptionally substituted with 1-5 R¹³, —NHheteroaryl optionallysubstituted with 1-10 R¹⁴; —C(═O)NHR¹⁵, —NH(C═O)R¹⁶, and —C(═O)R¹⁷;

R⁴ is selected from the group consisting of H, halide, CN, —OR¹⁸,—CH₂OH, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), -(5-9membered heteroaryl) optionally substituted with 1-10 R¹⁹; phenyloptionally substituted with 1-5 R²⁰, —NHphenyl optionally substitutedwith 1-5 R²¹, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R²², —C(═O)NHR²³, —NH(C═O)R²⁴, and —C(═O)R²⁵;

with the proviso that at least two of R², R³, and R⁴ are H;

each R⁵ is independently selected from the group consisting of —OR²⁶,-heterocyclyl optionally substituted with 1-10 R²⁷, and —NHheterocyclyloptionally substituted with 1-10 R²⁸;

each R⁶ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a carbonyl group;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

R⁷ is selected from the group consisting of H, unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl);

each R⁸ is independently selected from the group consisting of H,halide, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

R⁹ is —CH₂(6-membered heteroaryl) optionally substituted with 1-4 R³⁹;

R¹⁰ is selected from the group consisting of unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl);

each R¹¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R¹² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R¹³ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R¹⁴ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

R¹⁵ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R¹⁶ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R¹⁷ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R¹⁸ is selected from the group consisting of unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), and —(CH₂)_(p)carbocyclyl optionallysubstituted with 1-12 R³⁸;

each R¹⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R²² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

R²³ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R²⁴ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R²⁵ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

each R²⁶ is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²⁹ is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R³¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³³ is independently selected from the group consisting of halide,—OR⁴⁵, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁴ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁵ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰, and-heteroaryl optionally substituted with 1-10 R³⁹;

each R³⁶ is -heterocyclyl optionally substituted with 1-10 R⁴¹;

each R³⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸;

each R⁴⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R³⁸, and —(CH₂)_(p)heteroaryl optionally substituted with 1-10 R³⁹;

each R⁴¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-carbocyclyl optionally substituted with 1-12 R³⁸, and -heterocyclyloptionally substituted with 1-10 R³⁷;

alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R⁴⁵ is independently selected from the group consisting ofunsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each m is independently 1 to 6; and

each p is independently 0 or 1.

Some embodiments include stereoisomers and pharmaceutically acceptablesalts of a compound of Formula I. Some embodiments includepharmaceutically acceptable salts of a compound of Formula I.

Some embodiments include pro-drugs of a compound of Formula I.

Some embodiments of the present disclosure include pharmaceuticalcompositions comprising a compound of Formula I and a pharmaceuticallyacceptable carrier, diluent, or excipient.

Other embodiments disclosed herein include methods of inhibiting DYRK1Aby administering to a patient affected by a disorder or disease in whichDYRK1A overexpression is implicated, such as Alzheimer's Disease,Amyotrophic Lateral Sclerosis, CDKL5 Deficiency Disorder, Down Syndrome,Frontotemporal Dementia with Parkinsonism-17 (FTDP-17), Lewy bodydementia, Parkinson's Disease, Pick's Disease, and additional diseaseswith pronounced neurodegeneration such as Autism, Dementia, Epilepsy,Huntington's Disease, Multiple Sclerosis; diseases and disordersassociated with acquired brain injury such as Chronic TraumaticEncephalopathy, Traumatic Brain Injury, Tumor and Stroke.

Inhibitors of DYRK1A can also be used to treat tauopathies. Tauopathiesare neurodegenerative disorders characterized by the deposition ofabnormal tau protein in the brain. The spectrum of tau pathologiesexpands beyond the traditionally discussed disease forms like Pick'sdisease, progressive supranuclear palsy, corticobasal degeneration, andargyrophilic grain disease. Emerging entities and pathologies includeglobular glial tauopathies, primary age-related tauopathy, whichincludes neurofibrillary tangle dementia, chronic traumaticencephalopathy (CTE), frontotemporal lobar degeneration with tauinclusions (FTLD-tau), and aging-related tau astrogliopathy. Clinicalsymptoms include frontotemporal dementia, corticobasal syndrome,Richardson syndrome, parkinsonism, pure akinesia with gait freezing and,rarely, motor neuron symptoms or cerebellar ataxia (Handbook of ClinicalNeurology (2018), 145, 355-368 and Aging Cell (2019), 18(5), e13000).

Inhibitors of DYRK1A can also be used to treat disorders associated withabnormal folate/methionine metabolism.

Non-limiting examples of diseases which can be treated with thecompounds and compositions provided herein include a variety of cancers,diabetes, psoriasis, knee osteoarthritis, tendinopathy, humanimmunodeficiency virus type 1 (HIV-1), human cytomegalovirus (HCMV),hepatitis C virus (HCV), and herpes simplex virus 1 (HSV-1).

Some embodiments of the present disclosure include methods to preparecompounds of Formula I.

It is to be understood that both the foregoing general description andthe following detailed description are exemplary and explanatory onlyand are not restrictive of the disclosure, as claimed.

DETAILED DESCRIPTION

Provided herein are compositions and methods for inhibiting DYRK1A.

Some embodiments provided herein relate to a method for treating adisease including, but not limited to, neurological diseases ordisorders, cancers, cognitive deficits, knee osteoarthritis,tendinopathy, viral infections, unicellular parasite infections, andmotor deficits.

In some embodiments, non-limiting examples of a neurological disease ordisorder which can be treated with the compounds and compositionsprovided herein include, but are not limited to, Alzheimer's disease,amyotrophic lateral sclerosis, Down Syndrome, frontotemporal dementiawith Parkinsonism-17 (FTDP-17), Lewy body dementia, Parkinson's disease,Pick's disease tauopathies, and additional diseases with pronouncedneurodegeneration such as autism, dementia, epilepsy, Huntington'sdisease, multiple sclerosis; diseases and disorders associated withacquired brain injury such as Chronic Traumatic Encephalopathy,Traumatic Brain Injury, Tumor, and Stroke.

In some embodiments, non-limiting examples of cancers which can betreated with the compounds and compositions provided herein includesolid cancers (e.g., glioblastoma, ovarian, breast, and pancreaticcancers) and leukemias (e.g., acute lymphoblastic leukemia, acutemegakaryoblastic leukemia, and chronic myeloid leukemia).

In some embodiments, pharmaceutical compositions are provided that areeffective for treatment of a disease of an animal, e.g., a mammal,caused by DYRK1A overexpression. The composition includes apharmaceutically acceptable carrier and a compound as described herein.

Definitions

Unless defined otherwise, all technical and scientific terms used hereinhave the same meaning as is commonly understood by one of ordinary skillin the art to which this disclosure belongs. All patents, applications,published applications, and other publications are incorporated byreference in their entirety. In the event that there is a plurality ofdefinitions for a term herein, those in this section prevail unlessstated otherwise.

As used herein, “alkyl” means a branched, or straight chain chemicalgroup containing only carbon and hydrogen, such as methyl, ethyl,n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl,n-pentyl, iso-pentyl, sec-pentyl and neo-pentyl. Alkyl groups can eitherbe unsubstituted or substituted with one or more substituents. In someembodiments, alkyl groups include 1 to 9 carbon atoms (for example, 1 to6 carbon atoms, 1 to 4 carbon atoms, or 1 to 2 carbon atoms).

As used herein, “alkenyl” means a straight or branched chain chemicalgroup containing only carbon and hydrogen and containing at least onecarbon-carbon double bond, such as ethenyl, 1-propenyl, 2-propenyl,2-methyl-1-propenyl, 1-butenyl, 2-butenyl, and the like. In variousembodiments, alkenyl groups can either be unsubstituted or substitutedwith one or more substituents. Typically, alkenyl groups will comprise 2to 9 carbon atoms (for example, 2 to 6 carbon atoms, 2 to 4 carbonatoms, or 2 carbon atoms).

As used herein, “alkynyl” means a straight or branched chain chemicalgroup containing only carbon and hydrogen and containing at least onecarbon-carbon triple bond, such as ethynyl, 1-propynyl, 1-butynyl,2-butynyl, and the like. In various embodiments, alkynyl groups caneither be unsubstituted or substituted with one or more substituents.Typically, alkynyl groups will comprise 2 to 9 carbon atoms (forexample, 2 to 6 carbon atoms, 2 to 4 carbon atoms, or 2 carbon atoms).

As used herein, “alkylene” means a bivalent branched or straight chainchemical group containing only carbon and hydrogen, such as methylene,ethylene, n-propylene, iso-propylene, n-butylene, iso-butylene,sec-butylene, tert-butylene, n-pentylene, iso-pentylene, sec-pentyleneand neo-pentylene. Alkylene groups can either be unsubstituted orsubstituted with one or more substituents. In some embodiments, alkylenegroups include 1 to 9 carbon atoms (for example, 1 to 6 carbon atoms, 1to 4 carbon atoms, or 1 to 2 carbon atoms).

As used herein, “alkenylene” means a bivalent branched or straight chainchemical group containing only carbon and hydrogen and containing atleast one carbon-carbon double bond, such as ethenylene, 1-propenylene,2-propenylene, 2-methyl-1-propenylene, 1-butenylene, 2-butenylene, andthe like. In various embodiments, alkenylene groups can either beunsubstituted or substituted with one or more substituents. Typically,alkenylene groups will comprise 2 to 9 carbon atoms (for example, 2 to 6carbon atoms, 2 to 4 carbon atoms, or 2 carbon atoms).

As used herein, “alkynylene” means a bivalent branched or straight chainchemical group containing only carbon and hydrogen and containing atleast one carbon-carbon triple bond, such as ethynylene, 1-propynylene,1-butynylene, 2-butynylene, and the like. In various embodiments,alkynylene groups can either be unsubstituted or substituted with one ormore substituents. Typically, alkynylene groups will comprise 2 to 9carbon atoms (for example, 2 to 6 carbon atoms, 2 to 4 carbon atoms, or2 carbon atoms).

As used herein, “alkoxy” means an alkyl-O— group in which the alkylgroup is as described herein. Exemplary alkoxy groups include methoxy,ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, t-butoxy, pentoxy,hexoxy and heptoxy, and also the linear or branched positional isomersthereof.

As used herein, “haloalkoxy” means a haloalkyl-O— group in which thehaloalkyl group is as described herein. Exemplary haloalkoxy groupsinclude fluoromethoxy, difluoromethoxy, trifluoromethoxy, and also thelinear or branched positional isomers thereof.

As used herein, “carbocyclyl” means a cyclic ring system containing onlycarbon atoms in the ring system backbone, such as cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, and cyclohexenyl. Carbocyclyls mayinclude multiple fused rings. Carbocyclyls may have any degree ofsaturation provided that none of the rings in the ring system arearomatic. Carbocyclyl groups can either be unsubstituted or substitutedwith one or more substituents. In some embodiments, carbocyclyl groupsinclude 3 to 10 carbon atoms, for example, 3 to 6 carbon atoms.

As used herein, “aryl” means a mono-, bi-, tri- or polycyclic group withonly carbon atoms present in the ring backbone having 5 to 14 ringatoms, alternatively 5, 6, 9, or 10 ring atoms; and having 6, 10, or 14pi electrons shared in a cyclic array; wherein at least one ring in thesystem is aromatic. Aryl groups can either be unsubstituted orsubstituted with one or more substituents. Examples of aryl includephenyl, naphthyl, tetrahydronaphthyl, 2,3-dihydro-1H-indenyl, andothers. In some embodiments, the aryl is phenyl.

As used herein, “arylalkylene” means an aryl-alkylene-group in which thearyl and alkylene moieties are as previously described. In someembodiments, arylalkylene groups contain a C₁₋₄alkylene moiety.Exemplary arylalkylene groups include benzyl and 2-phenethyl.

As used herein, the term “heteroaryl” means a mono-, bi-, tri- orpolycyclic group having 5 to 14 ring atoms, alternatively 5, 6, 9, or 10ring atoms; and having 6, 10, or 14 pi electrons shared in a cyclicarray; wherein at least one ring in the system is aromatic, and at leastone ring in the system contains one or more heteroatoms independentlyselected from the group consisting of N, O, and S. Heteroaryl groups caneither be unsubstituted or substituted with one or more substituents.Examples of heteroaryl include thienyl, pyridinyl, furyl, oxazolyl,oxadiazolyl, pyrrolyl, imidazolyl, triazolyl, thiodiazolyl, pyrazolyl,isoxazolyl, thiadiazolyl, pyranyl, pyrazinyl, pyrimidinyl, pyridazinyl,triazinyl, thiazolyl benzothienyl, benzoxadiazolyl, benzofuranyl,benzimidazolyl, benzotriazolyl, cinnolinyl, indazolyl, indolyl,isoquinolinyl, isothiazolyl, naphthyridinyl, purinyl, thienopyridinyl,pyrido[2,3-d]pyrimidinyl, pyrrolo[2,3-b]pyridinyl, quinazolinyl,quinolinyl, thieno[2,3-c]pyridinyl, pyrazolo[3,4-b]pyridinyl,pyrazolo[3,4-c]pyridinyl, pyrazolo[4,3-c]pyridine,pyrazolo[4,3-b]pyridinyl, tetrazolyl, chromane,2,3-dihydrobenzo[b][1,4]dioxine, benzo[d][1,3]dioxole,2,3-dihydrobenzofuran, tetrahydroquinoline,2,3-dihydrobenzo[b][1,4]oxathiine , isoindoline, and others. In someembodiments, the heteroaryl is selected from thienyl, pyridinyl, furyl,pyrazolyl, imidazolyl, isoindolinyl, pyranyl, pyrazinyl, andpyrimidinyl.

As used herein, “halo”, “halide” or “halogen” is a chloro, bromo,fluoro, or iodo atom radical. In some embodiments, a halo is a chloro,bromo or fluoro. For example, a halide can be fluoro.

As used herein, “haloalkyl” means a hydrocarbon substituent, which is alinear or branched, alkyl, alkenyl or alkynyl substituted with one ormore chloro, bromo, fluoro, and/or iodo atom(s). In some embodiments, ahaloalkyl is a fluoroalkyls, wherein one or more of the hydrogen atomshave been substituted by fluoro. In some embodiments, haloalkyls are of1 to 3 carbons in length (e.g., 1 to 2 carbons in length or 1 carbon inlength). The term “haloalkylene” means a diradical variant of haloalkyl,and such diradicals may act as spacers between radicals, other atoms, orbetween a ring and another functional group.

As used herein, “heterocyclyl” means a nonaromatic cyclic ring systemcomprising at least one heteroatom in the ring system backbone.Heterocyclyls may include multiple fused rings such as bicyclic andspirocyclic heterocyclyls. Heterocyclyls may be substituted orunsubstituted with one or more substituents. In some embodiments,heterocycles have 3-11 members. In six membered monocyclic heterocycles,the heteroatom(s) are selected from one to three of O, N and S, andwherein when the heterocycle is five membered, it can have one or twoheteroatoms selected from O, N, and S. Examples of heterocyclyl includeazirinyl, aziridinyl, azetidinyl, oxetanyl, thietanyl,1,4,2-dithiazolyl, dihydropyridinyl, 1,3-dioxanyl, 1,4-dioxanyl,1,3-dioxolanyl, morpholinyl, thiomorpholinyl, piperazinyl, pyranyl,pyrrolidinyl, tetrahydrofuryl, tetrahydropyridinyl, oxazinyl, thiazinyl,thiinyl, thiazolidinyl, isothiazolidinyl, oxazolidinyl, isoxazolidinyl,piperidinyl, pyrazolidinyl imidazolidinyl, thiomorpholinyl, and others.In some embodiments, the heterocyclyl is selected from azetidinyl,morpholinyl, piperazinyl, pyrrolidinyl, and tetrahydropyridinyl.

As used herein, “monocyclic heterocyclyl” means a single nonaromaticcyclic ring comprising at least one heteroatom in the ring systembackbone. Heterocyclyls may be substituted or unsubstituted with one ormore substituents. In some embodiments, heterocycles have 3-7 members.In six membered monocyclic heterocycles, the heteroatom(s) are selectedfrom one to three of O, N and S, and wherein when the heterocycle isfive membered, it can have one or two heteroatoms selected from O, N,and S. Examples of monocyclic heterocyclyls include azirinyl,aziridinyl, azetidinyl, oxetanyl, thietanyl, 1,4,2-dithiazolyl,dihydropyridinyl, 1,3-dioxanyl, 1,4-dioxanyl, 1,3-dioxolanyl,morpholinyl, thiomorpholinyl, piperazinyl, pyranyl, pyrrolidinyl,tetrahydrofuryl, tetrahydropyridinyl, oxazinyl, thiazinyl, thiinyl,thiazolidinyl, isothiazolidinyl, oxazolidinyl, isoxazolidinyl,piperidinyl, pyrazolidinyl imidazolidinyl, thiomorpholinyl, and others.

As used herein, “bicyclic heterocyclyl” means a nonaromatic bicyclicring system comprising at least one heteroatom in the ring systembackbone. Bicyclic heterocyclyls may be substituted or unsubstitutedwith one or more substituents. In some embodiments, bicyclicheterocycles have 4-11 members with the heteroatom(s) being selectedfrom one to five of O, N and S. Examples of bicyclic heterocyclylsinclude 2-azabicyclo[1.1.0]butane, 2-azabicyclo[2.1.0]pentane,2-azabicyclo[1.1.1]pentane, 3-azabicyclo[3.1.0]hexane,5-azabicyclo[2.1.1]hexane, 3-azabicyclo[3.2.0]heptane,octahydrocyclopenta[c]pyrrole, 3-azabicyclo[4.1.0]heptane,7-azabicyclo[2.2.1]heptane, 6-azabicyclo[3.1.1]heptane,7-azabicyclo[4.2.0]octane, 2-azabicyclo[2.2.2]octane, and the like.

As used herein, “spirocyclic heterocyclyl” means a nonaromatic bicyclicring system comprising at least one heteroatom in the ring systembackbone and with the rings connected through just one atom. Spirocyclicheterocyclyls may be substituted or unsubstituted with one or moresubstituents. In some embodiments, spirocyclic heterocycles have 5-11members with the heteroatom(s) being selected from one to five of O, Nand S. Examples of spirocyclic heterocyclyls include2-azaspiro[2.2]pentane, 4-azaspiro[2.5]octane, 1-azaspiro[3.5]nonane,2-azaspiro[3.5]nonane, 7-azaspiro[3.5]nonane, 2-azaspiro[4.4]nonane,6-azaspiro[2.6]nonane, 1,7-diazaspiro[4.5]decane,2,5-diazaspiro[3.6]decane, and the like.

The term “substituted” refers to moieties having substituents replacinga hydrogen on one or more non-hydrogen atoms of the molecule. It will beunderstood that “substitution” or “substituted with” includes theimplicit proviso that such substitution is in accordance with permittedvalence of the substituted atom and the substituent, and that thesubstitution results in a stable compound, e.g., which does notspontaneously undergo transformation such as by rearrangement,cyclization, elimination, etc. Substituents can include, for example,—(C₁₋₉ alkyl) optionally substituted with one or more of hydroxyl, —NH₂,—NH(C₁₋₃ alkyl), and —N(C₁₋₃ alkyl)₂; —(C₁₋₉ haloalkyl); a halide; ahydroxyl; a carbonyl [such as —C(O)OR, and —C(O)R]; a thiocarbonyl [suchas —C(S)OR, —C(O)SR, and —C(S)R]; —(C₁₋₉ alkoxy) optionally substitutedwith one or more of halide, hydroxyl, —NH₂, —NH(C₁₋₃ alkyl), and —N(C₁₋₃alkyl)₂; —OPO(OH)₂; a phosphonate [such as —PO(OH)₂ and —PO(OR′)₂];—OPO(OR′)R″; —NRR′; —C(O)NRR′; —C(NR)NR′R″; —C(NR′)R″; a cyano; a nitro;an azido; —SH; —S—R; —OSO₂(OR); a sulfonate [such as —SO₂(OH) and—SO₂(OR)]; —SO₂NR′R″; and —SO₂R; in which each occurrence of R, R′ andR″ are independently selected from H; —(C₁₋₉ alkyl); C₆₋₁₀ aryloptionally substituted with 1-3 R″′; 5-10 membered heteroaryl havingfrom 1-4 heteroatoms independently selected from N, O, and S andoptionally substituted with 1-3 R″′; C₃₋₇ carbocyclyl optionallysubstituted with 1-3 R″′; and 3-8 membered heterocyclyl having from 1-4heteroatoms independently selected from N, O, and S and optionallysubstituted with 1-3 R′″; wherein each R″′ is independently selectedfrom —(C₁₋₆ alkyl), —(C₁₋₆ haloalkyl), a halide (e.g., F), a hydroxyl,—C(O)OR, —C(O)R, —(C₁₋₆ alkoxyl), —NRR′, —C(O)NRR′, and a cyano, inwhich each occurrence of R and R′ is independently selected from H and—(C₁₋₆ alkyl). In some embodiments, the substituent is selected from—(C₁₋₆ alkyl), —(C₁₋₆ haloalkyl), a halide (e.g., F), a hydroxyl,—C(O)OR, —C(O)R, —(C₁₋₆ alkoxyl), —NRR′, —C(O)NRR′, and a cyano, inwhich each occurrence of R and R′ is independently selected from H and—(C₁₋₆ alkyl).

As used herein, when two groups are indicated to be “linked” or “bonded”to form a “ring”, it is to be understood that a bond is formed betweenthe two groups and may involve replacement of a hydrogen atom on one orboth groups with the bond, thereby forming a carbocyclyl, heterocyclyl,aryl, or heteroaryl ring. The skilled artisan will recognize that suchrings can and are readily formed by routine chemical reactions. In someembodiments, such rings have from 3-7 members, for example, 5 or 6members.

The skilled artisan will recognize that some chemical structuresdescribed herein may be represented on paper by one or more otherresonance forms; or may exist in one or more other tautomeric forms,even when kinetically, the artisan recognizes that such tautomeric formsrepresent only a very small portion of a sample of such compound(s).Such compounds are clearly contemplated within the scope of thisdisclosure, though such resonance forms or tautomers are not explicitlyrepresented herein.

The compounds provided herein may encompass various stereochemicalforms. The compounds also encompass diastereomers as well as opticalisomers, e.g., mixtures of enantiomers including racemic mixtures, aswell as individual enantiomers and diastereomers, which arise as aconsequence of structural asymmetry in certain compounds. Separation ofthe individual isomers or selective synthesis of the individual isomersis accomplished by application of various methods which are well knownto practitioners in the art. Unless otherwise indicated, when adisclosed compound is named or depicted by a structure withoutspecifying the stereochemistry and has one or more chiral centers, it isunderstood to represent all possible stereoisomers of the compound.

The present disclosure includes all pharmaceutically acceptableisotopically labeled compounds of Formula I wherein one or more atomsare replaced by atoms having the same atomic number, but an atomic massor mass number different from the atomic mass or mass number whichpredominates in nature. Examples of isotopes suitable for inclusion inthe compounds of the disclosure include, but are not limited to,isotopes of hydrogen, such as ²H (deuterium) and ³H (tritium), isotopesof carbon, such as ¹¹C, ¹³C and ¹⁴C, isotopes of chlorine, such as ³⁶Cl,isotopes of fluorine, such as ¹⁸F, isotopes of iodine, such as ¹²³I and¹²⁵I, isotopes of nitrogen, such as ¹³N and ¹⁵N, isotopes of oxygen,such as ¹⁵O, ¹⁷O and ¹⁸O, isotopes of phosphorus, such as ³²P, andisotopes of sulfur, such as ³⁵S.

The term “administration” or “administering” refers to a method ofproviding a dosage of a compound or pharmaceutical composition to avertebrate or invertebrate, including a mammal, a bird, a fish, or anamphibian, where method of administration is, e.g., orally,subcutaneously, intravenously, intralymphatic, intranasally, topically,transdermally, intraperitoneally, intramuscularly, intrapulmonarilly,vaginally, rectally, ontologically, neuro-otologically, intraocularly,subconjuctivally, via anterior eye chamber injection, intravitreally,intraperitoneally, intrathecally, intracystically, intrapleurally, viawound irrigation, intrabuccally, intra-abdominally, intra-articularly,intra-aurally, intrabronchially, intracapsularly, intrameningeally, viainhalation, via endotracheal or endobronchial instillation, via directinstillation into pulmonary cavities, intraspinally, intrasynovially,intrathoracically, via thoracostomy irrigation, epidurally,intratympanically, intracisternally, intravascularly,intraventricularly, intraosseously, via irrigation of infected bone, orvia application as part of any admixture with a prosthetic device. Themethod of administration can vary depending on various factors, e.g.,the components of the pharmaceutical composition, the site of thedisease, the disease involved, and the severity of the disease.

A “diagnostic” as used herein is a compound, method, system, or devicethat assists in the identification or characterization of a health ordisease state. The diagnostic can be used in standard assays as is knownin the art.

The term “mammal” is used in its usual biological sense. Thus, itspecifically includes humans, cattle, horses, monkeys, dogs, cats, mice,rats, cows, sheep, pigs, goats, and non-human primates, but alsoincludes many other species.

The term “pharmaceutically acceptable carrier”, “pharmaceuticallyacceptable diluent” and “pharmaceutically acceptable excipient” includesany and all solvents, co-solvents, complexing agents, dispersion media,coatings, isotonic and absorption delaying agents and the like which arenot biologically or otherwise undesirable. The use of such media andagents for pharmaceutically active substances is well known in the art.Except insofar as any conventional media or agent is incompatible withthe active ingredient, its use in the therapeutic compositions iscontemplated. Supplementary active ingredients can also be incorporatedinto the compositions. In addition, various adjuvants such as arecommonly used in the art may be included. These and other such compoundsare described in the literature, e.g., in the Merck Index, Merck &Company, Rahway, N.J. Considerations for the inclusion of variouscomponents in pharmaceutical compositions are described, e.g., in Gilmanet al. (Eds.) (2010); Goodman and Gilman's: The Pharmacological Basis ofTherapeutics, 12th Ed., The McGraw-Hill Companies.

The term “pharmaceutically acceptable salt” refers to salts that retainthe biological effectiveness and properties of the compounds providedherein and, which are not biologically or otherwise undesirable. In manycases, the compounds provided herein are capable of forming acid and/orbase salts by virtue of the presence of amino and/or carboxyl groups orgroups similar thereto. Many such salts are known in the art, forexample, as described in WO 87/05297. Pharmaceutically acceptable acidaddition salts can be formed with inorganic acids and organic acids.Inorganic acids from which salts can be derived include, for example,hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid,phosphoric acid, and the like. Organic acids from which salts can bederived include, for example, acetic acid, propionic acid, glycolicacid, pyruvic acid, oxalic acid, maleic acid, malonic acid, succinicacid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamicacid, mandelic acid, methanesulfonic acid, ethanesulfonic acid,p-toluenesulfonic acid, salicylic acid, and the like. Pharmaceuticallyacceptable base addition salts can be formed with inorganic and organicbases. Inorganic bases from which salts can be derived include, forexample, sodium, potassium, lithium, ammonium, calcium, magnesium, iron,zinc, copper, manganese, aluminum, and the like; particularly preferredare the ammonium, potassium, sodium, calcium, and magnesium salts.Organic bases from which salts can be derived include, for example,primary, secondary, and tertiary amines, substituted amines includingnaturally occurring substituted amines, cyclic amines, basic ionexchange resins, and the like, specifically such as isopropylamine,trimethylamine, diethylamine, triethylamine, tripropylamine, andethanolamine.

“Patient” as used herein, means a human or a non-human mammal, e.g., adog, a cat, a mouse, a rat, a cow, a sheep, a pig, a goat, a non-humanprimate, or a bird, e.g., a chicken, as well as any other vertebrate orinvertebrate. In some embodiments, the patient is a human.

A “therapeutically effective amount” of a compound as provided herein isone which is sufficient to achieve the desired physiological effect andmay vary according to the nature and severity of the disease condition,and the potency of the compound. “Therapeutically effective amount” isalso intended to include one or more of the compounds of Formula I incombination with one or more other agents that are effective to treatthe diseases and/or conditions described herein. The combination ofcompounds can be a synergistic combination. Synergy, as described, forexample, by Chou and Talalay, Advances in Enzyme Regulation (1984), 22,27-55, occurs when the effect of the compounds when administered incombination is greater than the additive effect of the compounds whenadministered alone as a single agent. In general, a synergistic effectis most clearly demonstrated at sub-optimal concentrations of thecompounds. It will be appreciated that different concentrations may beemployed for prophylaxis than for treatment of an active disease. Thisamount can further depend upon the patient's height, weight, sex, age,and medical history.

A therapeutic effect relieves, to some extent, one or more of thesymptoms of the disease.

“Treat,” “treatment,” or “treating,” as used herein refers toadministering a compound or pharmaceutical composition as providedherein for therapeutic purposes. The term “therapeutic treatment” refersto administering treatment to a patient already suffering from a diseasethus causing a therapeutically beneficial effect, such as amelioratingexisting symptoms, ameliorating the underlying metabolic causes ofsymptoms, postponing, or preventing the further development of adisorder, and/or reducing the severity of symptoms that will or areexpected to develop.

“Drug-eluting” and/or controlled release as used herein refers to anyand all mechanisms, e.g., diffusion, migration, permeation, and/ordesorption by which the drug(s) incorporated in the drug-elutingmaterial pass therefrom over time into the surrounding body tissue.

“Drug-eluting material” and/or controlled release material as usedherein refers to any natural, synthetic, or semi-synthetic materialcapable of acquiring and retaining a desired shape or configuration andinto which one or more drugs can be incorporated and from whichincorporated drug(s) are capable of eluting over time.

“Elutable drug” as used herein refers to any drug or combination ofdrugs having the ability to pass over time from the drug-elutingmaterial in which it is incorporated into the surrounding areas of thebody.

Compounds

The compounds and compositions described herein can be used to inhibitDYRK1A for treating a disorder or disease in which DYRK1A overexpressionis implicated, such as in neurological diseases or disorders, cancers,cognitive deficits, knee osteoarthritis, tendinopathy, viral infections,unicellular parasite infections, and motor deficits.

Some embodiments of the present disclosure include compounds of FormulaI:

or salts, pharmaceutically acceptable salts, or prodrugs thereof,

wherein:

R¹ is pyridinyl substituted with 1-4 R⁵;

R² is selected from the group consisting of H, —OR⁷, 5-memberedheteroaryl optionally substituted with 1-3 R⁸, and —NHR⁹.

R³ is selected from the group consisting of H, CN, —CO₂H, —OR¹⁰,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R¹¹, -(5-9membered heteroaryl) optionally substituted with 1-10 R¹²; phenyloptionally substituted with 1-5 R¹³, —NHheteroaryl optionallysubstituted with 1-10 R¹⁴; —C(═O)NHR¹⁵, —NH(C═O)R¹⁶, and —C(═O)R¹⁷;

R⁴ is selected from the group consisting of H, halide, CN, —OR¹⁸,—CH₂OH, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), -(5-9membered heteroaryl) optionally substituted with 1-10 R¹⁹; phenyloptionally substituted with 1-5 R²⁰, —NHphenyl optionally substitutedwith 1-5 R²¹, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R²², —C(═O)NHR²³, —NH(C═O)R²⁴, and —C(═O)R²⁵;

with the proviso that at least two of R², R³, and R⁴ are H;

each R⁵ is independently selected from the group consisting of —OR²⁶,-heterocyclyl optionally substituted with 1-10 R²⁷, and —NHheterocyclyloptionally substituted with 1-10 R²⁸;

R⁷ is selected from the group consisting of H, unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl);

each R⁸ is independently selected from the group consisting of H,halide, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

R⁹ is —CH₂(6-membered heteroaryl) optionally substituted with 1-4 R³⁹;

R¹⁰ is selected from the group consisting of unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl);

each R¹¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R¹² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R¹³ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R¹⁴ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

R¹⁵ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R¹⁶ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R¹⁷ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R¹⁸ is selected from the group consisting of unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), and —(CH₂)_(p)carbocyclyl optionallysubstituted with 1-12 R³⁸;

each R¹⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R²² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

R²³ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R²⁴ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R²⁵ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

each R²⁶ is unsubstituted —(C₁₋₉ haloalkyl);

each R²⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸;

each p is independently 0 or 1; and

with the proviso that Formula I is not a structure selected from thegroup consisting of:

Some embodiments of the present disclosure include compounds of FormulaIa:

or salts, pharmaceutically acceptable salts, or prodrugs thereof,

wherein:

R¹ is selected from the heteroaryl group consisting of:

and optionally substituted with 1-10 R⁶; and

wherein a carbon atom on an aromatic ring of the heteroaryl form thebond with

each R⁶ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a carbonyl group;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R^(6a) is independently selected from the group consisting of—OR^(29a), —CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

each R²⁹ is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R^(29a) is -heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R³¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³³ is independently selected from the group consisting of halide,—OR⁴⁵, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁴ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁵ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰, and-heteroaryl optionally substituted with 1-10 R³⁹;

R³⁶ is -heterocyclyl optionally substituted with 1-10 R⁴¹;

each R³⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸;

each R⁴⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R³⁸, and —(CH₂)_(p)heteroaryl optionally substituted with 1-10 R³⁹;

each R⁴¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-carbocyclyl optionally substituted with 1-12 R³⁸, and -heterocyclyloptionally substituted with 1-10 R³⁷;

alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R⁴² is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R⁴⁵ is independently selected from the group consisting ofunsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each n is independently 0 to 3;

each m is independently 1 to 6;

each p is independently 0 or 1; and

with the proviso that Formula Ia is not a structure selected from thegroup consisting of:

Some embodiments of the present disclosure include compounds of FormulaIb:

or salts, pharmaceutically acceptable salts, or prodrugs thereof,

wherein:

R¹ is 7-14-membered heteroaryl optionally substituted with 1-10 R⁶;

with the proviso that when the heteroaryl is selected from the groupconsisting of

that the 2-position is substituted with R⁴²;

wherein a carbon atom on an aromatic ring of the heteroaryl form thebond with

R² is selected from the group consisting of H, —OR⁷, 5-memberedheteroaryl optionally substituted with 1-3 R⁸, and —NHR⁹;

R⁴ is selected from the group consisting of H, halide, CN, —OR¹⁸,—CH₂OH, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), -(5-9membered heteroaryl) optionally substituted with 1-10 R¹⁹; phenyloptionally substituted with 1-5 R²⁰, —NHphenyl optionally substitutedwith 1-5 R²¹, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R²², —C(═O)NHR²³, —NH(C═O)R²⁴, and —C(═O)R²⁵;

with the proviso that one of R² and R⁴ is H and the other of R² and R⁴is not H;

each R⁶ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a carbonyl group;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

R⁷ is selected from the group consisting of H, unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl);

each R⁸ is independently selected from the group consisting of H,halide, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

R⁹ is —CH₂(6-membered heteroaryl) optionally substituted with 1-4 R³⁹;

R¹⁸ is selected from the group consisting of unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), and —(CH₂)_(p)carbocyclyl optionallysubstituted with 1-12 R³⁸;

each R¹⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R²² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

R²³ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R²⁴ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R²⁵ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

each R²⁹ is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R³¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³³ is independently selected from the group consisting of halide,—OR⁴⁵, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁴ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁵ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰, and-heteroaryl optionally substituted with 1-10 R³⁹;

each R³⁶ is -heterocyclyl optionally substituted with 1-10 R⁴¹;

each R³⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸;

each R⁴⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R³⁸, and —(CH₂)_(p)heteroaryl optionally substituted with 1-10 R³⁹;

each R⁴¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-carbocyclyl optionally substituted with 1-12 R³⁸, and -heterocyclyloptionally substituted with 1-10 R³⁷;

alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R⁴² is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R⁴⁵ is independently selected from the group consisting ofunsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each m is independently 1 to 6;

each p is independently 0 or 1; and

with the proviso that Formula Ib is not a structure selected from thegroup consisting of:

Some embodiments of the present disclosure include compounds of FormulaIc:

or salts, pharmaceutically acceptable salts, or prodrugs thereof,

wherein:

R¹ is 7-14-membered heteroaryl optionally substituted with 1-10 R⁶;

wherein a carbon atom on an aromatic ring of the heteroaryl form thebond with

R² is selected from the group consisting of H, —OR⁷, 5-memberedheteroaryl optionally substituted with 1-3 R⁸, and —NHR⁹,

each R⁶ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a carbonyl group;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

R⁷ is selected from the group consisting of H, unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl);

each R⁸ is independently selected from the group consisting of H,halide, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

R⁹ is —CH₂(6-membered heteroaryl) optionally substituted with 1-4 R³⁹;

each R²⁹ is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R³¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³³ is independently selected from the group consisting of halide,—OR⁴⁵, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁴ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁵ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰, and-heteroaryl optionally substituted with 1-10 R³⁹;

each R³⁶ is -heterocyclyl optionally substituted with 1-10 R⁴¹;

each R³⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸;

each R⁴⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R³⁸, and —(CH₂)_(p)heteroaryl optionally substituted with 1-10 R³⁹;

each R⁴¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-carbocyclyl optionally substituted with 1-12 R³⁸, and -heterocyclyloptionally substituted with 1-10 R³⁷;

alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R⁴⁵ is independently selected from the group consisting ofunsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each m is independently 1 to 6;

each p is independently 0 or 1; and

with the proviso that Formula Ic is not a structure selected from thegroup consisting of:

Some embodiments of the present disclosure include compounds of FormulaIc:

or salts, pharmaceutically acceptable salts, or prodrugs thereof,

wherein:

R¹ is selected from the heteroaryl group consisting of:

and optionally substituted with 1-10 R⁶; and

is optionally substituted with 1-4 R^(6a);

wherein a carbon atom on an aromatic ring of the heteroaryl form thebond with

R² is selected from the group consisting of H, —OR⁷, 5-memberedheteroaryl optionally substituted with 1-3 R⁸, and —NHR⁹,

each R⁶ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a carbonyl group;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R^(6a) is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

R⁷ is selected from the group consisting of H, unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl);

each R⁸ is independently selected from the group consisting of H,halide, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

R⁹ is —CH₂(6-membered heteroaryl) optionally substituted with 1-4 R³⁹;

each R²⁹ is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R³¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³³ is independently selected from the group consisting of halide,—OR⁴⁵, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁴ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁵ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰, and-heteroaryl optionally substituted with 1-10 R³⁹;

each R³⁶ is -heterocyclyl optionally substituted with 1-10 R⁴¹;

each R³⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸;

each R⁴⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R³⁸, and —(CH₂)_(p)heteroaryl optionally substituted with 1-10 R³⁹;

each R⁴¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-carbocyclyl optionally substituted with 1-12 R³⁸, and -heterocyclyloptionally substituted with 1-10 R³⁷;

alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R⁴⁵ is independently selected from the group consisting ofunsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each m is independently 1 to 6; and

each p is independently 0 or 1.

Some embodiments of the present disclosure include compounds of FormulaId:

or salts, pharmaceutically acceptable salts, or prodrugs thereof,

wherein:

R¹ is 7-14-membered heteroaryl optionally substituted with 1-10 R⁶;

with the proviso that when the heteroaryl is selected from the groupconsisting of

that the 2-position is substituted with R⁴²;

wherein a carbon atom on an aromatic ring of the heteroaryl form thebond with

R⁴ is selected from the group consisting of halide, CN, —OR¹⁸, —CH₂OH,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), -(5-9membered heteroaryl) optionally substituted with 1-10 R¹⁹; phenyloptionally substituted with 1-5 R²⁰, —NHphenyl optionally substitutedwith 1-5 R²¹, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R²², —C(═O)NHR²³, —NH(C═O)R²⁴, and —C(═O)R²⁵;

each R⁶ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a carbonyl group;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

R¹⁸ is selected from the group consisting of unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), and —(CH₂)_(p)carbocyclyl optionallysubstituted with 1-12 R³⁸;

each R¹⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R²² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

R²³ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R²⁴ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R²⁵ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

each R²⁹ is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R³¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³³ is independently selected from the group consisting of halide,—OR⁴⁵, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁴ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁵ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰, and-heteroaryl optionally substituted with 1-10 R³⁹;

each R³⁶ is -heterocyclyl optionally substituted with 1-10 R⁴¹;

each R³⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸;

each R⁴⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R³⁸, and —(CH₂)_(p)heteroaryl optionally substituted with 1-10 R³⁹;

each R⁴¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-carbocyclyl optionally substituted with 1-12 R³⁸, and -heterocyclyloptionally substituted with 1-10 R³⁷;

alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R⁴² is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R⁴⁵ is independently selected from the group consisting ofunsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each m is independently 1 to 6;

each p is independently 0 or 1; and

with the proviso that Formula Id is not a structure selected from thegroup consisting of:

Some embodiments of the present disclosure include compounds of FormulaId:

or salts, pharmaceutically acceptable salts, or prodrugs thereof,

wherein:

R¹ is selected from the heteroaryl group consisting of:

and optionally substituted with 1-10 R⁶;

wherein a carbon atom on an aromatic ring of the heteroaryl form thebond with

R⁴ is selected from the group consisting of halide, CN, —OR¹⁸, —CH₂OH,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), -(5-9membered heteroaryl) optionally substituted with 1-10 R¹⁹; phenyloptionally substituted with 1-5 R²⁰, —NHphenyl optionally substitutedwith 1-5 R²¹, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R²², —C(═O)NHR²³, —NH(C═O)R²⁴, —C(═O)R²⁵;

each R⁶ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, —C(═O)R³⁶;

alternatively, two R⁶ attached to the same carbon atom to form acarbonyl group;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

R¹⁸ is selected from the group consisting of unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), and —(CH₂)_(p)carbocyclyl optionallysubstituted with 1-12 R³⁸;

each R¹⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R²¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R²² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

R²³ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R²⁴ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R²⁵ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

each R²⁹ is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R³¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³³ is independently selected from the group consisting of halide,—OR⁴⁵, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁴ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁵ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰, and-heteroaryl optionally substituted with 1-10 R³⁹;

each R³⁶ is -heterocyclyl optionally substituted with 1-10 R⁴¹;

each R³⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸;

each R⁴⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R³⁸, and —(CH₂)_(p)heteroaryl optionally substituted with 1-10 R³⁹;

each R⁴¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-carbocyclyl optionally substituted with 1-12 R³⁸, and -heterocyclyloptionally substituted with 1-10 R³⁷;

alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R⁴² is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R⁴⁵ is independently selected from the group consisting ofunsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each m is independently 1 to 6;

each p is independently 0 or 1; and

with the proviso that Formula Id is not a structure selected from thegroup consisting of:

Some embodiments of the present disclosure include compounds of FormulaIe:

or salts, pharmaceutically acceptable salts, or prodrugs thereof,

wherein:

R¹ is selected from the heteroaryl group consisting of:

and optionally substituted with 1-10 R⁶; and

with the proviso that when R¹ is

R³ is not halide or methyl;

wherein a carbon atom on an aromatic ring of the heteroaryl form thebond with

R³ is selected from the group consisting of halide, CN, —CO₂H, —OR¹⁰,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₁₋₉haloalkyl),—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R¹¹, -(5-9membered heteroaryl) optionally substituted with 1-10 R¹²; phenyloptionally substituted with 1-5 R¹³, —NHheteroaryl optionallysubstituted with 1-10 R¹⁴; —C(═O)NHR¹⁵, —NH(C═O)R¹⁶, and —C(═O)R¹⁷;

each R⁶ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉alkynyl), unsubstituted —(C₁₋₉haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a carbonyl group;

alternatively, two R⁶ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R^(6a) is independently selected from the group consisting ofhalide, unsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

each R^(6b) is independently selected from the group consisting of—OR²⁹, —CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶;

R¹⁰ is selected from the group consisting of unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl);

each R¹¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R¹² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R¹³ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R¹⁴ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

R¹⁵ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R¹⁶ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

R¹⁷ is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹;

each R²⁹ is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R³¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³³ is independently selected from the group consisting of halide,—OR⁴⁵, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each R³⁴ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁵ are independently selected from the group consisting of H,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰, and-heteroaryl optionally substituted with 1-10 R³⁹;

each R³⁶ is -heterocyclyl optionally substituted with 1-10 R⁴¹;

each R³⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸;

each R⁴⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R³⁸, and —(CH₂)_(p)heteroaryl optionally substituted with 1-10 R³⁹;

each R⁴¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-carbocyclyl optionally substituted with 1-12 R³⁸, and -heterocyclyloptionally substituted with 1-10 R³⁷;

alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸;

each R⁴² is independently selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R⁴³ is H;

each R⁴⁴ is independently selected from the group consisting of H,unsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);

each R⁴⁵ is independently selected from the group consisting ofunsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷;

each n is independently 0 to 6;

each m is independently 1 to 6;

each p is independently 0 or 1; and

with the proviso that Formula Ie is not a structure selected from thegroup consisting of:

Some embodiments of the present disclosure include compounds of FormulaI:

or salts, pharmaceutically acceptable salts, or prodrugs thereof.

Some embodiments of the present disclosure include compounds of FormulaIa:

or salts, pharmaceutically acceptable salts, or prodrugs thereof.

Some embodiments of the present disclosure include compounds of FormulaIb:

or salts, pharmaceutically acceptable salts, or prodrugs thereof.

Some embodiments of the present disclosure include compounds of FormulaIc:

or salts, pharmaceutically acceptable salts, or prodrugs thereof.

Some embodiments of the present disclosure include compounds of FormulaId:

or salts, pharmaceutically acceptable salts, or prodrugs thereof.

Some embodiments of the present disclosure include compounds of FormulaIe:

or salts, pharmaceutically acceptable salts, or prodrugs thereof.

In some embodiments of Formula I, R¹ is selected from the groupconsisting of 6-membered heteroaryl optionally substituted with 1-4(e.g., 1-3, 1-2, 1) R⁵ and 7-14-membered heteroaryl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R⁶.

In some embodiments of Formula I, R¹ is pyridinyl substituted with 1-4(e.g., 1-3, 1-2, 1) R⁵.

In some embodiments of Formula I, R¹ is 4-pyridine substituted with 1R⁵.

In some embodiments of Formula Ia, R¹ is selected from the heteroarylgroup consisting of:

and optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5,1-4, 1-3, 1-2, 1) R⁶; and

In some embodiments of Formulas Ib, Ic, and Id, R¹ is 7-14-memberedheteroaryl optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6,1-5, 1-4, 1-3, 1-2, 1) R⁶.

In some embodiments of Formulas Ib and Id, there is the proviso thatwhen the heteroaryl is selected from the group consisting of

that the 2-position is substituted with R⁴².

In some embodiments of Formula Ic, R¹ is selected from the heteroarylgroup consisting of:

and optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5,1-4, 1-3, 1-2, 1) R⁶; and

is optionally substituted with 1-4 (e.g., 1-3, 1-2, 1) R^(6a).

In some embodiments of Formula Id, R¹ is selected from the heteroarylgroup consisting of:

and optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5,1-4, 1-3, 1-2, 1) R⁶.

In some embodiments of Formula Ie, R¹ is selected from the heteroarylgroup consisting of:

and optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5,1-4, 1-3, 1-2, 1) R⁶; and

and

In some embodiments of Formula Ie, there is the proviso that when R¹ is

R³ is not halide or methyl.

In some embodiments of Formulas Ia, Ib, and Ie, R¹ is selected from thegroup consisting of:

optionally substituted with 1-2 R⁶.

In some embodiments of Formulas Ia, Ib, and Ie, R¹ is selected from thegroup consisting of:

optionally substituted with 1-2 R⁶.

In some embodiments of Formula I, a carbon atom on an aromatic ring ofthe heteroaryl R¹ group form the bond with

In some embodiments of Formula Ia, a carbon atom on an aromatic ring ofthe heteroaryl R¹ group form the bond with

In some embodiments of Formula Ib, a carbon atom on an aromatic ring ofthe heteroaryl R¹ group form the bond with

In some embodiments of Formula Ic, a carbon atom on an aromatic ring ofthe heteroaryl R¹ group form the bond with

In some embodiments of Formula Id, a carbon atom on an aromatic ring ofthe heteroaryl R¹ group form the bond with

In some embodiments of Formula Ie, a carbon atom on an aromatic ring ofthe heteroaryl R¹ group form the bond with

In some embodiments of Formulas I, Ib, and Ic, R² is selected from thegroup consisting of H, —OR⁷, and 5-membered heteroaryl optionallysubstituted with 1-3 R⁸, and —NHR⁹.

In some embodiments of Formulas I and Ie, R³ is selected from the groupconsisting of H, halide (e.g., F, Cl, Br, I), CN, —CO₂H, —OR¹⁰,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 (e.g., 1-9, 1-8,1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R¹¹, -(5-9 membered heteroaryl)optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4,1-3, 1-2, 1) R¹²; phenyl optionally substituted with 1-5 (e.g., 1-4,1-3, 1-2, 1) R¹³, —NHheteroaryl optionally substituted with 1-10 (e.g.,1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R¹⁴; —C(═O)NHR¹⁵,—NH(C═O)R¹⁶, and —C(═O)R¹⁷.

In some embodiments of Formulas I, Ib, and Ie, R³ and R⁴ are H and R² isselected from the group consisting of —OMe and a 5-membered heteroaryloptionally substituted with 1 R⁸.

In some embodiments of Formulas I, Ib, and Ie, R⁴ is H and R² isselected from the group consisting of —OMe and a 5-membered heteroaryloptionally substituted with 1 R⁸.

In some embodiments of Formulas I and Ib, R² and R⁴ are H and R³ isselected from the group consisting of -heterocyclyl optionallysubstituted with 1 R¹¹, -(5-6 membered heteroaryl) optionallysubstituted with 1-2 R¹²; —C(═O)NHR¹⁵, —NH(C═O)R¹⁶, and —C(═O)R¹⁷.

In some embodiments of Formula Ie, R³ is selected from the groupconsisting of -heterocyclyl optionally substituted with 1 R¹¹, -(5-6membered heteroaryl) optionally substituted with 1-2 R¹²; —C(═O)NHR¹⁵,—NH(C═O)R¹⁶, and —C(═O)R¹⁷.

In some embodiments of Formula I, R³ is selected from the groupconsisting of H, CN, —CO₂H, —OR¹⁰, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), —(CH₂)_(p)heterocyclyl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R¹¹, -(5-9 membered heteroaryl) optionally substituted with 1-10 (e.g.,1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R¹²; phenyl optionallysubstituted with 1-5 R¹³, —NHheteroaryl optionally substituted with 1-10(e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R¹⁴; —C(═O)NHR¹⁵,—NH(C═O)R¹⁶, and —C(═O)R¹⁷.

In some embodiments of Formulas I, Ib, and Id, R⁴ is selected from thegroup consisting of H, halide (e.g., F, Cl, Br, I), CN, —OR¹⁸, —CH₂OH,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), -(5-9membered heteroaryl) optionally substituted with 1-10 (e.g., 1-9, 1-8,1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R¹⁹; phenyl optionally substituted with1-5 (e.g., 1-4, 1-3, 1-2, 1) R²⁰, —NHphenyl optionally substituted with1-5 (e.g., 1-4, 1-3, 1-2, 1) R²¹, —(CH₂)_(p)carbocyclyl optionallysubstituted with 1-12 (e.g., 1-11, 1-10, 1-9, 1-8, 1-7, 1-6, 1-5, 1-4,1-3, 1-2, 1) R²², —C(═O)NHR²³, —NH(C═O)R²⁴, and —C(═O)R²⁵.

In some embodiments of Formulas I, Ib, and Ie, R² and R³ are H and R⁴ isselected from the group consisting of -carbocyclyl, —C(═O)NHR²³, and—NH(C═O)R²⁴.

In some embodiments of Formulas I, Ib, and Ie, R² is H and R⁴ isselected from the group consisting of -carbocyclyl, —C(═O)NHR²³, and—NH(C═O)R²⁴.

In some embodiments of Formula I, there is the proviso that at least twoof R², R³, and R⁴ are H.

In some embodiments of Formula Ib, there is the proviso that one of R²and R⁴ is H and the other of R² and R⁴ is not H.

In some embodiments of Formula I, each R⁵ is independently selected fromthe group consisting of —OR²⁶, -heterocyclyl optionally substituted with1-10 R²⁷, and —NHheterocyclyl optionally substituted with 1-10 (e.g.,1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R²⁸.

In some embodiments of Formula I, each R⁵ is independently selected fromthe group consisting of —OMe and -heterocyclyl optionally substitutedwith 1 R²⁷.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R⁶ isindependently selected from the group consisting of halide (e.g., F, Cl,Br, I), unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 (e.g., 1-9, 1-8,1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁰, —NHheterocyclyl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³¹, -heteroaryl optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7,1-6, 1-5, 1-4, 1-3, 1-2, 1) R³²; —NHheteroaryl optionally substitutedwith 1-10 R³³; —NHCH₂heteroaryl optionally substituted with 1-10 (e.g.,1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³³; ⁻CH₂N(R³⁴)₂,—C(═O)N(R³⁵)₂, and —C(═O)R³⁶.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, two R⁶attached to the same carbon atom are taken together to form a carbonylgroup.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, two R⁶attached to the same carbon atom are taken together to form a ring whichis selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁷ and -carbocyclyl optionally substituted with 1-12 (e.g., 1-11, 1-10,1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁸.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R⁶ isindependently selected from the group consisting of unsubstituted —(C₁₋₃alkyl), -heterocyclyl optionally substituted with 1 R³⁰, -(5-6 memberedheteroaryl) optionally substituted with 1-2 R³², and —C(═O)NHR³⁵.

In some embodiments of Formula Ia, each R^(6a) is independently selectedfrom the group consisting of —OR^(29a), —CH₂OH, -heterocyclyl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁰, —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶.

In some embodiments of Formula Ic, each R^(6a) is independently selectedfrom the group consisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted—(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉haloalkyl), —OR²⁹, —CH₂OH, -heterocyclyl optionally substituted with1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁰,—NHheterocyclyl optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7,1-6, 1-5, 1-4, 1-3, 1-2, 1) R³¹, -heteroaryl optionally substituted with1-10 R³²; —NHheteroaryl optionally substituted with 1-10 (e.g., 1-9,1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³³; —NHCH₂heteroaryl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶.

In some embodiments of Formula Ie, each R^(6a) is independently selectedfrom the group consisting of halide (e.g., F, Cl, Br, I), unsubstituted—(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹, —CH₂OH, -heterocyclyloptionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4,1-3, 1-2, 1) R³⁰, —NHheterocyclyl optionally substituted with 1-10(e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³¹, -heteroaryloptionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4,1-3, 1-2, 1) R³²; —NHheteroaryl optionally substituted with 1-10 (e.g.,1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³³; —NHCH₂heteroaryloptionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4,1-3, 1-2, 1) R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶.

In some embodiments of Formula Ie, each R^(6b) is independently selectedfrom the group consisting of —OR²⁹, —CH₂OH, -heterocyclyl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁰, —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶.

In some embodiments of Formulas I, Ib, and Ic, R⁷ is selected from thegroup consisting of H, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl).

In some embodiments of Formulas I, Ib, and Ic, each R⁸ is independentlyselected from the group consisting of H, halide (e.g., F, Cl, Br, I),unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ib, and Ic, R⁹ is —CH₂(6-memberedheteroaryl) optionally substituted with 1-4 R³⁹.

In some embodiments of Formulas I and Ie, R¹⁰ is selected from the groupconsisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl).

In some embodiments of Formulas I and Ie, each R¹¹ is independentlyselected from the group consisting of halide (e.g., F, Cl, Br, I),unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I and Ie, each R¹² is independentlyselected from the group consisting of halide (e.g., F, Cl, Br, I),unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7,1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷.

In some embodiments of Formulas I and Ie, each R¹³ is independentlyselected from the group consisting of halide (e.g., F, Cl, Br, I),unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7,1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷.

In some embodiments of Formulas I and Ie, each R¹⁴ is independentlyselected from the group consisting of halide (e.g., F, Cl, Br, I),unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7,1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷.

In some embodiments of Formulas I and Ie, R¹⁵ is selected from the groupconsisting of -heterocyclyl optionally substituted with 1-10 (e.g., 1-9,1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷ and -heteroaryl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁹.

In some embodiments of Formulas I and Ie, R¹⁶ is selected from the groupconsisting of -heterocyclyl optionally substituted with 1-10 (e.g., 1-9,1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷ and -heteroaryl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁹.

In some embodiments of Formulas I and Ie, R¹⁷ is selected from the groupconsisting of -heterocyclyl optionally substituted with 1-10 (e.g., 1-9,1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷ and -heteroaryl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁹.

In some embodiments of Formulas I, Ib, and Id, R¹⁸ is selected from thegroup consisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉haloalkyl), and —(CH₂)_(p)carbocyclyl optionally substituted with 1-12(e.g., 1-11, 1-10, 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁸.

In some embodiments of Formulas I, Ib, and Id, each R¹⁹ is independentlyselected from the group consisting of halide (e.g., F, Cl, Br, I),unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ib, and Id, each R²⁰ is independentlyselected from the group consisting of halide (e.g., F, Cl, Br, I),unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ib, and Id, each R²¹ is independentlyselected from the group consisting of halide (e.g., F, Cl, Br, I),unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7,1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷.

In some embodiments of Formulas I, Ib, and Id, each R²² is independentlyselected from the group consisting of halide (e.g., F, Cl, Br, I),unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ib, and Id, R²³ is selected from thegroup consisting of -heterocyclyl optionally substituted with 1-10(e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷ and -heteroaryloptionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4,1-3, 1-2, 1) R³⁹.

In some embodiments of Formulas I, Ib, and Id, R²⁴ is selected from thegroup consisting of -heterocyclyl optionally substituted with 1-10(e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷ and -heteroaryloptionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4,1-3, 1-2, 1) R³⁹.

In some embodiments of Formulas I, Ib, and Id, R²⁵ is selected from thegroup consisting of -heterocyclyl optionally substituted with 1-10(e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷ and -heteroaryloptionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4,1-3, 1-2, 1) R³⁹.

In some embodiments of Formula I, each R²⁶ is independently selectedfrom the group consisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted—(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl).

In some embodiments of Formula I, each R²⁶ is unsubstituted —(C₁₋₉haloalkyl).

In some embodiments of Formula I, each R²⁷ is independently selectedfrom the group consisting of halide (e.g., F, Cl, Br, I), unsubstituted—(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formula I, each R²⁸ is independently selectedfrom the group consisting of halide (e.g., F, Cl, Br, I), unsubstituted—(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R²⁹ isindependently selected from the group consisting of unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), and -heterocyclyl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁷.

In some embodiments of Formula Ia, each R^(29a) is -heterocyclyloptionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4,1-3, 1-2, 1) R³⁷.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R³⁰ isindependently selected from the group consisting of halide (e.g., F, Cl,Br, I), unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, two R³⁰attached to the same carbon atom are taken together to form a ring whichis selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁷ and -carbocyclyl optionally substituted with 1-12 (e.g., 1-11, 1-10,1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁸.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R³¹ isindependently selected from the group consisting of halide (e.g., F, Cl,Br, I), unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R³² isindependently selected from the group consisting of halide (e.g., F, Cl,Br, I), unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R³³ isindependently selected from the group consisting of halide (e.g., F, Cl,Br, I), —OR⁴⁵, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉haloalkyl), and -heterocyclyl optionally substituted with 1-10 (e.g.,1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R³⁴ areindependently selected from the group consisting of H, unsubstituted—(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R³⁵ areindependently selected from the group consisting of H, unsubstituted—(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); —(CH₂)_(p)heterocyclyloptionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4,1-3, 1-2, 1) R⁴⁰, and -heteroaryl optionally substituted with 1-10(e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁹.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R³⁶ is-heterocyclyl optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7,1-6, 1-5, 1-4, 1-3, 1-2, 1) R⁴¹.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R³⁷ isindependently selected from the group consisting of halide (e.g., F, Cl,Br, I), unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R³⁸ isindependently selected from the group consisting of halide (e.g., F, Cl,Br, I), unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R³⁹ isindependently selected from the group consisting of halide (e.g., F, Cl,Br, I), unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 (e.g., 1-9, 1-8, 1-7,1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁷, and -heteroaryl optionally substitutedwith 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁸.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R⁴⁰ isindependently selected from the group consisting of halide (e.g., F, Cl,Br, I), unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),—(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12(e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁸, and—(CH₂)_(p)heteroaryl optionally substituted with 1-10 (e.g., 1-9, 1-8,1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁹.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R⁴¹ isindependently selected from the group consisting of halide (e.g., F, Cl,Br, I), unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-carbocyclyl optionally substituted with 1-12 (e.g., 1-11, 1-10, 1-9,1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁸, and -heterocyclyl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁷.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, two R⁴¹attached to the same carbon atom are taken together to form a ring whichis selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁷ and -carbocyclyl optionally substituted with 1-12 (e.g., 1-11, 1-10,1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1) R³⁸.

In some embodiments of Formulas Ia, Ib, Id, and Ie, each R⁴² isindependently selected from the group consisting of unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl).

In some embodiments of Formula Ie, each R⁴³ is H.

In some embodiments of Formula Ie, each R⁴⁴ is independently selectedfrom the group consisting of H, unsubstituted —(C₂₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), andunsubstituted —(Cl-9 haloalkyl).

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each R⁴⁵ isindependently selected from the group consisting of unsubstituted —(C₂₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), and -heterocyclyl optionallysubstituted with 1-10 (e.g., 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, 1)R³⁷.

In some embodiments of Formula Ia, each n is independently 0 or 3.

In some embodiments of Formula Ie, each n is independently 0 or 6.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each m isindependently 1 or 6.

In some embodiments of Formulas I, Ia, Ib, Ic, Id, and Ie, each p isindependently 0 or 1.

In some embodiments, there is the proviso that Formula I is not astructure selected from the group consisting of:

In some embodiments, there is the proviso that Formula Ia is not astructure selected from the group consisting of:

In some embodiments, there is the proviso that Formula Ib is not astructure selected from the group consisting of:

In some embodiments, there is the proviso that Formula Ic is not astructure selected from the group consisting of:

In some embodiments, there is the proviso that Formula Id is not astructure selected from the group consisting of:

In some embodiments, there is the proviso that Formula Ie is not astructure selected from the group consisting of:

In some embodiments, each m is independently 1 to 6 (e.g., 1-5, 1-4,1-3, 1-2, 1).

In some embodiments, each n is independently 0 to 6 (e.g., 0-5, 0-4,0-3, 0-2, 0-1, 0).

Illustrative compounds of Formulas I, Ia, Ib, Ic, Id, and Ie, are shownin Table 1.

TABLE 1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

67

68

69

70

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

87

88

89

90

91

92

93

94

95

96

97

98

99

100

101

102

103

104

105

106

107

108

109

110

111

112

113

114

115

116

117

118

119

120

121

122

123

124

125

126

127

128

129

130

131

132

133

134

135

136

137

138

139

140

141

142

143

144

145

146

147

148

149

150

151

152

153

154

155

156

157

158

159

160

161

162

163

164

165

166

167

168

169

170

171

172

173

174

175

176

177

178

179

180

181

182

183

184

185

186

187

188

189

190

191

192

193

194

195

196

197

198

199

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209

210

211

212

213

214

215

216

217

218

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220

221

222

223

224

225

226

227

228

229

230

231

232

233

234

235

236

237

238

239

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248

249

250

251

252

253

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260

261

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273

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275

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288

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315

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451

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531

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541

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729

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731

732

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764

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767

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769

770

771

772

773

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775

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780

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784

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790

791

792

793

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799

800

801

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807

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809

810

811

812

813

814

815

816

817

818

819

820

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825

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830

831

832

833

834

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837

838

839

840

841

842

843

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850

851

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865

866

867

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870

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895

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901

902

903

904

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908

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910

911

912

913

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920

921

922

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924

925

926

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930

931

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938

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940

941

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950

951

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961

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971

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981

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987

988

989

990

991

992

993

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996

997

998

999

1000

1001

1002

1003

1004

1005

1006

1007

1008

1009

1010

1011

1012

1013

1014

1015

1016

1017

1018

1019

1020

1021

1022

1023

1024

1025

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1038

1039

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1100

1101

1102

1103

1104

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1110

1111

1112

1113

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1117

1118

1119

1120

1121

1122

1123

1124

1125

1126

1127

1128

1129

1130

1131

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1133

1134

1135

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1177

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1190

1191

1192

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1195

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1198

1199

1200

1201

1202

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1211

1212

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1234

1235

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Administration and Pharmaceutical Compositions

Some embodiments include pharmaceutical compositions comprising: (a) atherapeutically effective amount of a compound provided herein, or itscorresponding enantiomer, diastereoisomer or tautomer, orpharmaceutically acceptable salt; and (b) a pharmaceutically acceptablecarrier.

The compounds provided herein may also be useful in combination(administered together or sequentially) with other known agents.

Non-limiting examples of diseases which can be treated with acombination of a compound of Formulas I, Ia, Ib, Ic, Id, and Ie, andanother active agent are colorectal cancer, ovarian cancer,hepatocellular carcinoma, head and neck squamous cell carcinoma, acutelymphoblastic leukemia (ALL), pancreatic cancer, brain tumors, acutemegakaryoblastic leukemia (AMKL), and osteoarthritis. For example, acompound of Formulas I, Ia, Ib, Ic, Id, and Ie can be combined with oneor more chemotherapeutic compounds.

In some embodiments, hepatocellular carcinoma can be treated with acombination of a compound of Formulas I, Ia, Ib, Ic, Id, and Ie, and oneor more of the following drugs/therapies: sorafenib (Nexavar®);regorafenib (Stivarga®, Regonix®), nivolumab (Opdivo®); lenvatinib(Lenvima®); Pembrolizumab (Keytruda®); cabozantinib (Cometriq®,Cabometyx®); 5-fluorouracil (5-FU®); ramucirumab (Cyramza®); combinationof gemcitabine and oxaliplatin (GEMOX). Other therapies that can beperformed in combination with a compound of Formulas I, Ia, Ib, Ic, Id,and Ie are i) transcatheter arterial chemoembolization (TACE) incombination with doxorubicin (DOXIL®), cisplatin, or mitomycin C(Mitosol®, Mutamycin®, Jelmyto®); ii) low-dose brachytherapy.

In some embodiments, head and neck squamous cell carcinoma can betreated with a combination of a compound of Formulas I, Ia, Ib, Ic, Id,and Ie, and one or more of the following drugs/therapies: TransOralRobotic Surgery (TORS); TORS with radiation therapy; larotrectinib(Vitrakvi®); EGFR inhibitors, e.g., erlotinib (Tarceva®), osimertinib(Tagrisso®), neratinib (Nerlynx®), gefitinib (Iressa®), cetuximab(Erbitux®), panitumumab (Vectibix®), dacomitinib (Vizimpro®), lapatinib(Tykerb®), necitumumab (Portrazza), and vandetanib (Caprelsa®).

In some embodiments, acute lymphoblastic leukemia (ALL) can be treatedwith a combination of a compound of Formulas I, Ia, Ib, Ic, Id, and Ie,and one or more of the following drugs/therapies: remission inductiontherapy; consolidation therapy; nelarabine (Arranon®); AsparaginaseErwinia Chrysanthemi (Erwinaze®); Asparaginase Erwinia Chrysanthemi(Recombinant)-rywn (Rylaze®); calaspargase Pegol-mknl (Asparlas®);inotuzumab ozogamicin (Besponsa®); blinatumomab (Blincyto®);daunorubicin hydrochloride (Cerubidine®); clofarabine (Clolar®);cyclophosphamide; methotrexate sodium (Trexall®); cytarabine(Cytosar-U®); dasatinib (Sprycel®); dexamethasone; imatinib mesylate(Gleevec®); ponatinib hydrochloride (Iclusig®); mercaptopurine(Purinethol®, Purixan®); tisagenlecleucel (Kymriah®); vincristinesulfate liposome (Marqibo®); pegaspargase (Oncaspar®); prednisone;daunorubicin hydrochloride (Rubidomycin®); and vincristine sulfate.

In some embodiments, pancreatic cancer can be treated with a combinationof a compound of Formulas I, Ia, Ib, Ic, Id, and Ie, and one or more ofthe following drugs/therapies: ablation and embolization treatment;gemcitabine (Gemzar®); 5-fluorouracil (5-FU®); oxaliplatin (Eloxatin®);albumin-bound paclitaxel (Abraxane®); capecitabine (Xeloda®); cisplatin;irinotecan (Camptosar®); liposomal Irinotecan (Onivyde®); paclitaxel(Taxol®), and docetaxel (Taxotere®).

In some embodiments, brain tumors can be treated with a combination of acompound of Formulas I, Ia, Ib, Ic, Id, and Ie, and one or more of thefollowing drugs/therapies: carmustine can be administered by way of agliadel wafer; for glioblastoma and high-grade glioma, radiation therapywith daily low-dose temozolomide (Temodar®) followed by monthly doses oftemozolomide after radiation therapy for 6 months to 1 year; lomustine(Gleostine®), procarbazine (Matulane®), and vincristine (Vincasar®),have been used along with radiation therapy; anti-angiogenesis therapywith bevacizumab (Avastin®, Mvasi®); and targeted therapy usinglarotrectinib (Vitrakvi®).

In some embodiments, acute megakaryoblastic leukemia (AMKL) can betreated with a combination of a compound of Formulas I, Ia, Ib, Ic, Id,and Ie, and one or more of the following drugs/therapies: cytarabine(Cytosar-U®), etoposide (Vepesid®), and anthracycline drugs.Anthracyclines include daunorubicin (Cerubidine®), idarubicin(Idamycin®), and mitoxantrone (Novantrone®).

In some embodiments, acute myeloid leukemia (AML) can be treated with acombination of a compound of Formulas I, Ia, Ib, Ic, Id, and Ie, and oneor more of the following drugs/therapies: venetoclax and hypomethylatingagents (e.g., decitabine, azacitidine), induction chemotherapy(cytarabine and an anthracycline (e.g., daunorubicin or idarubicin),all-trans-retinoic acid (ATRA) and either arsenic trioxide (ATO)monotherapy or an anthracycline), consolidation therapy (cytarabine).

In some embodiments, myelodysplastic syndrome (MDS) can be treated witha combination of a compound of Formulas I, Ia, Ib, Ic, Id, and Ie, andone or more of the following drugs/therapies: 5-azacytidine, decitabine,lenalidomide, and decitabine/cedazuridine (Inqovi®).

In some embodiments, colorectal cancer can be treated with a combinationof a compound of Formulas I, Ia, Ib, Ic, Id, and Ie, and one or more ofthe following drugs: 5-Fluorouracil (5-FU), which can be administeredwith the vitamin-like drug leucovorin (also called folinic acid);capecitabine (XELODA®), irinotecan (CAMPOSTAR®), oxaliplatin(ELOXATIN®). Examples of combinations of these drugs which could befurther combined with a compound of Formulas I, Ia, Ib, Ic, Id, and Ieare FOLFOX (5-FU, leucovorin, and oxaliplatin), FOLFIRI (5-FU,leucovorin, and irinotecan), FOLFOXIRI (leucovorin, 5-FU, oxaliplatin,and irinotecan) and CapeOx (Capecitabine and oxaliplatin). For rectalcancer, chemo with 5-FU or capecitabine combined with radiation may begiven before surgery (neoadjuvant treatment).

In some embodiments, ovarian cancer can be treated with a combination ofa compound of Formulas I, Ia, Ib, Ic, Id, and Ie, and one or more of thefollowing drugs: Topotecan, Liposomal doxorubicin (DOXIL®), Gemcitabine(GEMZAR®), Cyclophosphamide (CYTOXAN®), Vinorelbine (NAVELBINE®),Ifosfamide (IFEX®), Etoposide (VP-16), Altretamine (HEXALEN®),Capecitabine (XELODA®), Irinotecan (CPT-11, CAMPTOSAR®), Melphalan,Pemetrexed (ALIMTA®) and Albumin bound paclitaxel (nab-paclitaxel,ABRAXANE®). Examples of combinations of these drugs which could befurther combined with a compound of Formulas I, Ia, Ib, Ic, Id, and Ieare TIP (paclitaxel [Taxol], ifosfamide, and cisplatin), VeIP(vinblastine, ifosfamide, and cisplatin) and VIP (etoposide [VP-16],ifosfamide, and cisplatin). Ovarian cancer can also be treated with acombination of a compound of Formula (I) and immune checkpoint blockade(ICB) therapy.

In some embodiments, a compound of Formulas I, Ia, Ib, Ic, Id, and Iecan be used to treat cancer in combination with any of the followingmethods: (a) Hormone therapy such as aromatase inhibitors, LHRH[luteinizing hormone-releasing hormone] analogs and inhibitors, andothers; (b) Ablation or embolization procedures such as radiofrequencyablation (RFA), ethanol (alcohol) ablation, microwave thermotherapy andcryosurgery (cryotherapy); (c) Chemotherapy using alkylating agents suchas cisplatin and carboplatin, oxaliplatin, mechlorethamine,cyclophosphamide, chlorambucil and ifosfamide; (d) Chemotherapy usinganti-metabolites such as azathioprine and mercaptopurine; (e)Chemotherapy using plant alkaloids and terpenoids such as vincaalkaloids (i.e. Vincristine, Vinblastine, Vinorelbine and Vindesine) andtaxanes; (f) Chemotherapy using podophyllotoxin, etoposide, teniposideand docetaxel; (g) Chemotherapy using topoisomerase inhibitors such asirinotecan, topotecan, amsacrine, etoposide, etoposide phosphate, andteniposide; (h) Chemotherapy using cytotoxic antibiotics such asactinomycin, anthracyclines, doxorubicin, daunorubicin, valrubicin,idarubicin, epirubicin, bleomycin, plicamycin and mitomycin; (i)Chemotherapy using tyrosine-kinase inhibitors such as Imatinib mesylate(GLEEVEC®, also known as STI-571), Gefitinib (Iressa, also known asZD1839), Erlotinib (marketed as TARCEVA®), Bortezomib (VELCADE®),tamoxifen, tofacitinib, crizotinib, Bcl-2 inhibitors (e.g. obatoclax,navitoclax (ABT-263), oblimersen (G3139), venetoclax (ABT-199),Gossypol), PARP inhibitors (e.g. Iniparib, Olaparib, Rucaparib,Niraparib, Talazoparib), PI3K inhibitors (e.g. perifosine in a phase IIItrial), VEGF Receptor 2 inhibitors (e.g. Apatinib), AN-152, (AEZS-108),Braf inhibitors (e.g. vemurafenib, dabrafenib and LGX818), MEKinhibitors (e.g. trametinib and MEK162), CDK inhibitors, (e.g.PD-0332991), salinomycin and Sorafenib; (j) Chemotherapy usingmonoclonal antibodies such as Rituximab (marketed as MABTHERA® orRITUXAN®), Trastuzumab (Herceptin also known as ErbB2), Cetuximab(marketed as ERBITUX®), and Bevacizumab (marketed as AVASTIN®); (k)Chemotherapy using KRAS G12C inhibitors such as sotorasib (Lumakras® andLumykras®), adagrasib (MRTX849), and ARS-3248 (Wellspring Biosciences);(l) Chemotherapy using checkpoint inhibitor therapy such as Ipilimumab(Yervoy®), Nivolumab (Opdivo®), Pembrolizumab (Keytruda), Atezolizumab(Tecentriq®), Avelumab (Bavencio), Durvalumab (Imfinzi), Cemiplimab(Libtayo®), and Spartalizumab (PDR001); (m) Chemotherapy usingantibody-drug conjugates (ADC) such as Gemtuzumab ozogamicin,Brentuximab vedotin, Trastuzumab emtansine, Inotuzumab ozogamicin,Polatuzumab vedotin, Enfortumab vedotin, Trastuzumab deruxtecan,Sacituzumab govitecan, Belantamab mafodotin, Moxetumomab pasudotox, andLoncastuximab tesirine; (n) Chemotherapy using proteasome inhibitorssuch as carfilzomib, lactacystin, disulfiram, salinosporamide A(marizomib), oprozomib, delanzomib, epoxomicin, MG132, β-hydroxyβ-methylbutyric acid (HMB), bortezomib, ixazomib (alone or in incombination with lenalidomide and dexamethasone); and (o) radiationtherapy.

In some embodiments, a compound of Formulas I, Ia, Ib, Ic, Id, and Ie,can be used to treat diabetes mellitus in combination with any of thefollowing methods: (a) injections of insulin; (b) biguanides such asmetformin (Glucophage), phenformin (DBI), and buformin; (c)thiazolidinediones (TZDs) such as rosiglitazone (Avandia), pioglitazone(Actos), and yroglitazone (Rezulin); (d) lyn kinase activators such asglimepiride (Amaryl®) and tolimidone (MLR-1023); (e) secretagogues suchas sulfonylureas (non-limiting examples are acetohexamide, carbutamide,chlorpropamide, glycyclamide (tolcyclamide), metahexamide, tolazamide,tolbutamide, glibenclamide (glyburide), glibornuride, gliclazide,glipizide, gliquidone, glisoxepide, glyclopyramide, and glimepiride) andmeglitinides (nonlimiting examples are repaglinide (Prandin),nateglinide (Starlix), and mitiglinide (Glufast)); (f) alpha-glucosidaseinhibitors such as acarbose (Glucobay, Precose, Prandase), miglitol(Glyset), and voglibose; (g) injectable incretin mimetics such asglucagon-like peptide-1 (GLP-1) and gastric inhibitory peptide(glucose-dependent insulinotropic peptide, GIP), nonlimiting examples ofinjectable glucagon-like peptide (GLP) analogs and agonists areexenatide (Exendin-4, marketed as Byetta), liraglutide (Victoza,Saxenda), taspoglutide, lixisenatide (Lyxumia), Semaglutide (Ozempic,Rybelsus), dulaglutide (Trulicity), albiglutide (Tanzeum), nonlimitingexamples of dipeptidyl peptidase-4 (DPP-4) inhibitors are sitagliptin(Januvia), vildagliptin (Galvus), saxagliptin (Onglyza), linagliptin(Tradjenta), gemigliptin (Zemiglo), anagliptin (Suiny), teneligliptin(Tenelia), alogliptin (Nesina, Vipidia, Kazano, Vipidomet (withmetformin), Oseni, Incresync (with pioglitazone)), trelagliptin(Zafatek, Wedica), omarigliptin (MK-3102), evogliptin (Suganon,Evodine), gosogliptin (Saterex), and dutogliptin; (h) injectable amylinanalogues such as pramlintide (Symlin); (i) glycosurics (SGLT2inhibitors) such as canagliflozin (Invokana, Sulisent, Prominad),dapagliflozin (Forxiga, Farxiga, Edistride), empagliflozin (Jardiance,Sciampa-M), ertugliflozin (Steglatro), ipragliflozin (Suglat),luseogliflozin (Lusefi), remogliflozin etabonate (pro-drug ofremogliflozin), sergliflozin etabonate (GW869682X), sotagliflozin(Zynquista), and tofogliflozin (CSG452).

In some embodiments, a compound of Formulas I, Ia, Ib, Ic, Id, and Iecan be used to treat osteoarthritis in combination with any of thefollowing methods: (d) injections of a Wnt signaling pathway inhibitor(e.g. lorecivivint); (a) Nonsteroidal anti-inflammatory drugs (NSAIDs)such as ibuprofen, naproxen, aspirin and acetaminophen; (b) physicaltherapy; (c) injections of corticosteroid medications; (d) injections ofhyaluronic acid derivatives (e.g. Hyalgan, Synvisc); (e) narcotics, likecodeine; (f) in combination with braces and/or shoe inserts or anydevice that can immobilize or support your joint to help you keeppressure off it (e.g., splints, braces, shoe inserts or other medicaldevices); (g) realigning bones (osteotomy); (h) joint replacement(arthroplasty); and (i) in combination with a chronic pain class.

In some embodiments, a compound of Formulas I, Ia, Ib, Ic, Id, and Iecan be used to treat Alzheimer's disease in combination with aducanumab(Aduhelm™); acetylcholinesterase inhibitors, e.g., tacrine, rivastigmine(Exelon®), galantamine (Razadyne® and GalantaMind™), and donepezil(Aricept®); and memantine (Axura®, Ebixa®, Namenda®).

Administration of the compounds disclosed herein or the pharmaceuticallyacceptable salts thereof can be via any of the accepted modes ofadministration, including, but not limited to, orally, subcutaneously,intravenously, intranasally, topically, transdermally,intraperitoneally, intramuscularly, intrapulmonarilly, vaginally,rectally, ontologically, neuro-otologically, intraocularly,subconjuctivally, via anterior eye chamber injection, intravitreally,intraperitoneally, intrathecally, intracystically, intrapleurally, viawound irrigation, intrabuccally, intra-abdominally, intra-articularly,intra-aurally, intrabronchially, intracapsularly, intrameningeally, viainhalation, via endotracheal or endobronchial instillation, via directinstillation into pulmonary cavities, intraspinally, intrasynovially,intrathoracically, via thoracostomy irrigation, epidurally,intratympanically, intracisternally, intravascularly,intraventricularly, intraosseously, via irrigation of infected bone, orvia application as part of any admixture with a prosthetic devices. Insome embodiments, the administration method includes oral or parenteraladministration.

Compounds provided herein intended for pharmaceutical use may beadministered as crystalline or amorphous products. Pharmaceuticallyacceptable compositions may include solid, semi-solid, liquid,solutions, colloidal, liposomes, emulsions, suspensions, complexes,coacervates and aerosols. Dosage forms, such as, e.g., tablets,capsules, powders, liquids, suspensions, suppositories, aerosols,implants, controlled release, or the like. They may be obtained, forexample, as solid plugs, powders, or films by methods such asprecipitation, crystallization, milling, grinding, supercritical fluidprocessing, coacervation, complex coacervation, encapsulation,emulsification, complexation, freeze drying, spray drying, orevaporative drying. Microwave or radio frequency drying may be used forthis purpose. The compounds can also be administered in sustained orcontrolled release dosage forms, including depot injections, osmoticpumps, pills (tablets and or capsules), transdermal (includingelectrotransport) patches, implants, and the like, for prolonged and/ortimed, pulsed administration at a predetermined rate.

The compounds can be administered either alone or in combination with aconventional pharmaceutical carrier, excipient, or the like.Pharmaceutically acceptable excipients include, but are not limited to,ion exchangers, alumina, aluminum stearate, lecithin, self-emulsifyingdrug delivery systems (SEDDS) such as d-α-tocopherol polyethylene glycol1000 succinate, surfactants used in pharmaceutical dosage forms such asTweens, poloxamers or other similar polymeric delivery matrices, serumproteins, such as human serum albumin, buffer substances such asphosphates, tris, glycine, sorbic acid, potassium sorbate, partialglyceride mixtures of saturated vegetable fatty acids, water, salts orelectrolytes, such as protamine sulfate, disodium hydrogen phosphate,potassium hydrogen phosphate, sodium-chloride, zinc salts, colloidalsilica, magnesium trisilicate, polyvinyl pyrrolidone, cellulose-basedsubstances, polyethylene glycol, sodium carboxymethyl cellulose,polyacrylates, waxes, polyethylene-polyoxypropylene-block polymers, andwool fat. Cyclodextrins such as α-, β, and γ-cyclodextrin, or chemicallymodified derivatives such as hydroxyalkylcyclodextrins, including 2- and3-hydroxypropyl-β-cyclodextrins, or other solubilized derivatives canalso be used to enhance delivery of compounds described herein. Dosageforms or compositions containing a compound as described herein in therange of 0.005% to 100% with the balance made up from non-toxic carriermay be prepared. The contemplated compositions may contain 0.001%-100%of a compound provided herein, in one embodiment 0.1-95%, in anotherembodiment 75-85%, in a further embodiment 20-80%. Actual methods ofpreparing such dosage forms are known, or will be apparent, to thoseskilled in this art; for example, see Remington: The Science andPractice of Pharmacy, 22^(nd) Edition (Pharmaceutical Press, London, UK.2012).

In one embodiment, the compositions will take the form of a unit dosageform such as a pill or tablet and thus the composition may contain,along with a compound provided herein, a diluent such as lactose,sucrose, dicalcium phosphate, or the like; a lubricant such as magnesiumstearate or the like; and a binder such as starch, gum acacia,polyvinylpyrrolidine, gelatin, cellulose, cellulose derivatives, or thelike. In another solid dosage form, a powder, marume, solution orsuspension (e.g., in propylene carbonate, vegetable oils, PEG's,poloxamer 124 or triglycerides) is encapsulated in a capsule (gelatin orcellulose base capsule). Unit dosage forms in which one or morecompounds provided herein or additional active agents are physicallyseparated are also contemplated; e.g., capsules with granules (ortablets in a capsule) of each drug; two-layer tablets; two-compartmentgel caps, etc. Enteric coated or delayed release oral dosage forms arealso contemplated.

Liquid pharmaceutically administrable compositions can, for example, beprepared by dissolving, dispersing, etc. a compound provided herein andoptional pharmaceutical adjuvants in a carrier (e.g., water, saline,aqueous dextrose, glycerol, glycols, ethanol, or the like) to form asolution, colloid, liposome, emulsion, complexes, coacervate orsuspension. If desired, the pharmaceutical composition can also containminor amounts of nontoxic auxiliary substances such as wetting agents,emulsifying agents, co-solvents, solubilizing agents, pH bufferingagents and the like (e.g., sodium acetate, sodium citrate, cyclodextrinderivatives, sorbitan monolaurate, triethanolamine acetate,triethanolamine oleate, and the like).

In some embodiments, the unit dosage of compounds of Formulas I, Ia, Ib,Ic, Id, and Ie is about 0.25 mg/Kg to about 50 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 0.25 mg/Kg to about 20 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 0.50 mg/Kg to about 19 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 0.75 mg/Kg to about 18 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 1.0 mg/Kg to about 17 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 1.25 mg/Kg to about 16 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 1.50 mg/Kg to about 15 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 1.75 mg/Kg to about 14 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 2.0 mg/Kg to about 13 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 3.0 mg/Kg to about 12 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 4.0 mg/Kg to about 11 mg/Kg in humans.

In some embodiments, the unit dosage of compounds of Formula Formulas I,Ia, Ib, Ic, Id, and Ie is about 5.0 mg/Kg to about 10 mg/Kg in humans.

In some embodiments, the compositions are provided in unit dosage formssuitable for single administration.

In some embodiments, the compositions are provided in unit dosage formssuitable for twice a day administration.

In some embodiments, the compositions are provided in unit dosage formssuitable for three times a day administration.

Injectables can be prepared in conventional forms, either as liquidsolutions, colloid, liposomes, complexes, coacervate or suspensions, asemulsions, or in solid forms suitable for reconstitution in liquid priorto injection. The percentage of a compound provided herein contained insuch parenteral compositions is highly dependent on the specific naturethereof, as well as the activity of the compound and the needs of thepatient. However, percentages of active ingredient of 0.01% to 10% insolution are employable and could be higher if the composition is asolid or suspension, which could be subsequently diluted to the abovepercentages.

In some embodiments, the composition comprises about 0.1-10% of theactive agent in solution.

In some embodiments, the composition comprises about 0.1-5% of theactive agent in solution.

In some embodiments, the composition comprises about 0.1-4% of theactive agent in solution.

In some embodiments, the composition comprises about 0.15-3% of theactive agent in solution.

In some embodiments, the composition comprises about 0.2-2% of theactive agent in solution.

In some embodiments, the compositions are provided in dosage formssuitable for continuous dosage by intravenous infusion over a period ofabout 1-96 hours.

In some embodiments, the compositions are provided in dosage formssuitable for continuous dosage by intravenous infusion over a period ofabout 1-72 hours.

In some embodiments, the compositions are provided in dosage formssuitable for continuous dosage by intravenous infusion over a period ofabout 1-48 hours.

In some embodiments, the compositions are provided in dosage formssuitable for continuous dosage by intravenous infusion over a period ofabout 1-24 hours.

In some embodiments, the compositions are provided in dosage formssuitable for continuous dosage by intravenous infusion over a period ofabout 1-12 hours.

In some embodiments, the compositions are provided in dosage formssuitable for continuous dosage by intravenous infusion over a period ofabout 1-6 hours.

In some embodiments, these compositions can be administered byintravenous infusion to humans at doses of about 5 mg/m² to about 300mg/m².

In some embodiments, these compositions can be administered byintravenous infusion to humans at doses of about 5 mg/m² to about 200mg/m².

In some embodiments, these compositions can be administered byintravenous infusion to humans at doses of about 5 mg/m² to about 100mg/m².

In some embodiments, these compositions can be administered byintravenous infusion to humans at doses of about 10 mg/m² to about 50mg/m².

In some embodiments, these compositions can be administered byintravenous infusion to humans at doses of about 50 mg/m² to about 200mg/m².

In some embodiments, these compositions can be administered byintravenous infusion to humans at doses of about 75 mg/m² to about 175mg/m².

In some embodiments, these compositions can be administered byintravenous infusion to humans at doses of about 100 mg/m² to about 150mg/m².

It is to be noted that concentrations and dosage values may also varydepending on the specific compound and the severity of the condition tobe alleviated. It is to be further understood that for any particularpatient, specific dosage regimens should be adjusted over time accordingto the individual need and the professional judgment of the personadministering or supervising the administration of the compositions, andthat the concentration ranges set forth herein are exemplary only andare not intended to limit the scope or practice of the claimedcompositions.

In one embodiment, the compositions can be administered to therespiratory tract (including nasal and pulmonary) e.g., through anebulizer, metered-dose inhalers, atomizer, mister, aerosol, dry powderinhaler, insufflator, liquid instillation or other suitable device ortechnique.

In some embodiments, aerosols intended for delivery to the nasal mucosaare provided for inhalation through the nose. For optimal delivery tothe nasal cavities, inhaled particle sizes of about 5 to about 100microns are useful, with particle sizes of about 10 to about 60 micronsbeing preferred. For nasal delivery, a larger inhaled particle size maybe desired to maximize impaction on the nasal mucosa and to minimize orprevent pulmonary deposition of the administered formulation. In someembodiments, aerosols intended for delivery to the lung are provided forinhalation through the nose or the mouth. For delivery to the lung,inhaled aerodynamic particle sizes of about less than 10 μm are useful(e.g., about 1 to about 10 microns). Inhaled particles may be defined asliquid droplets containing dissolved drug, liquid droplets containingsuspended drug particles (in cases where the drug is insoluble in thesuspending medium), dry particles of pure drug substance, drug substanceincorporated with excipients, liposomes, emulsions, colloidal systems,coacervates, aggregates of drug nanoparticles, or dry particles of adiluent which contain embedded drug nanoparticles.

In some embodiments, compounds of Formulas I, Ia, Ib, Ic, Id, and Iedisclosed herein intended for respiratory delivery (either systemic orlocal) can be administered as aqueous formulations, as non-aqueoussolutions, or suspensions, as suspensions or solutions in halogenatedhydrocarbon propellants with or without alcohol, as a colloidal system,as emulsions, coacervates, or as dry powders. Aqueous formulations maybe aerosolized by liquid nebulizers employing either hydraulic orultrasonic atomization or by modified micropump systems (like the softmist inhalers, the Aerodose® or the AERx® systems). Propellant-basedsystems may use suitable pressurized metered-dose inhalers (pMDIs). Drypowders may use dry powder inhaler devices (DPIs), which are capable ofdispersing the drug substance effectively. A desired particle size anddistribution may be obtained by choosing an appropriate device.

In some embodiments, the compositions of Formulas I, Ia, Ib, Ic, Id, andIe disclosed herein can be administered to the ear by various methods.For example, a round window catheter (e.g., U.S. Pat. Nos. 6,440,102 and6,648,873) can be used.

Alternatively, formulations can be incorporated into a wick for usebetween the outer and middle ear (e.g., U.S. Pat. No. 6,120,484) orabsorbed to collagen sponge or other solid support (e.g., U.S. Pat. No.4,164,559).

If desired, formulations of the disclosure can be incorporated into agel formulation (e.g., U.S. Pat. Nos. 4,474,752 and 6,911,211).

In some embodiments, compounds of Formulas I, Ia, Ib, Ic, Id, and Iedisclosed herein intended for delivery to the ear can be administeredvia an implanted pump and delivery system through a needle directly intothe middle or inner ear (cochlea) or through a cochlear implant styletelectrode channel or alternative prepared drug delivery channel such asbut not limited to a needle through temporal bone into the cochlea.

Other options include delivery via a pump through a thin film coatedonto a multichannel electrode or electrode with a specially imbeddeddrug delivery channel (pathways) carved into the thin film for thispurpose. In other embodiments the acidic or basic solid compound ofFormulas I, Ia, Ib, Ic, Id, and Ie can be delivered from the reservoirof an external or internal implanted pumping system.

Formulations of the disclosure also can be administered to the ear byintratympanic injection into the middle ear, inner ear, or cochlea(e.g., U.S. Pat. No. 6,377,849 and Ser. No. 11/337,815).

Intratympanic injection of therapeutic agents is the technique ofinjecting a therapeutic agent behind the tympanic membrane into themiddle and/or inner ear. In one embodiment, the formulations describedherein are administered directly onto the round window membrane viatranstympanic injection. In another embodiment, the ion channelmodulating agent auris-acceptable formulations described herein areadministered onto the round window membrane via a non-transtympanicapproach to the inner ear. In additional embodiments, the formulationdescribed herein is administered onto the round window membrane via asurgical approach to the round window membrane comprising modificationof the crista fenestrae cochleae.

In some embodiments, the compounds of Formulas I, Ia, Ib, Ic, Id, and Ieare formulated in rectal compositions such as enemas, rectal gels,rectal foams, rectal aerosols, suppositories, jelly suppositories, orretention enemas, containing conventional suppository bases such ascocoa butter or other glycerides, as well as synthetic polymers such aspolyvinylpyrrolidone, PEG (like PEG ointments), and the like.

Suppositories for rectal administration of the drug (either as asolution, colloid, suspension or a complex) can be prepared by mixing acompound provided herein with a suitable non-irritating excipient thatis solid at ordinary temperatures but liquid at the rectal temperatureand will therefore melt or erode/dissolve in the rectum and release thecompound. Such materials include cocoa butter, glycerinated gelatin,hydrogenated vegetable oils, poloxamers, mixtures of polyethyleneglycols of various molecular weights and fatty acid esters ofpolyethylene glycol. In suppository forms of the compositions, alow-melting wax such as, but not limited to, a mixture of fatty acidglycerides, optionally in combination with cocoa butter, is firstmelted.

Solid compositions can be provided in various different types of dosageforms, depending on the physicochemical properties of the compoundprovided herein, the desired dissolution rate, cost considerations, andother criteria. In one of the embodiments, the solid composition is asingle unit. This implies that one unit dose of the compound iscomprised in a single, physically shaped solid form or article. In otherwords, the solid composition is coherent, which is in contrast to amultiple unit dosage form, in which the units are incoherent.

Examples of single units which may be used as dosage forms for the solidcomposition include tablets, such as compressed tablets, film-likeunits, foil-like units, wafers, lyophilized matrix units, and the like.In one embodiment, the solid composition is a highly porous lyophilizedform. Such lyophilizates, sometimes also called wafers or lyophilizedtablets, are particularly useful for their rapid disintegration, whichalso enables the rapid dissolution of the compound.

On the other hand, for some applications the solid composition may alsobe formed as a multiple unit dosage form as defined above. Examples ofmultiple units are powders, granules, microparticles, pellets,mini-tablets, beads, lyophilized powders, and the like. In oneembodiment, the solid composition is a lyophilized powder. Such adispersed lyophilized system comprises a multitude of powder particles,and due to the lyophilization process used in the formation of thepowder, each particle has an irregular, porous microstructure throughwhich the powder is capable of absorbing water very rapidly, resultingin quick dissolution. Effervescent compositions are also contemplated toaid the quick dispersion and absorption of the compound.

Another type of multiparticulate system which is also capable ofachieving rapid drug dissolution is that of powders, granules, orpellets from water-soluble excipients which are coated with a compoundprovided herein so that the compound is located at the outer surface ofthe individual particles. In this type of system, the water-soluble lowmolecular weight excipient may be useful for preparing the cores of suchcoated particles, which can be subsequently coated with a coatingcomposition comprising the compound and, for example, one or moreadditional excipients, such as a binder, a pore former, a saccharide, asugar alcohol, a film-forming polymer, a plasticizer, or otherexcipients used in pharmaceutical coating compositions.

Also provided herein are kits. Typically, a kit includes one or morecompounds or compositions as described herein. In certain embodiments, akit can include one or more delivery systems, e.g., for delivering oradministering a compound as provided herein, and directions for use ofthe kit (e.g., instructions for treating a patient). In anotherembodiment, the kit can include a compound or composition as describedherein and a label that indicates that the contents are to beadministered to a patient with cancer. In another embodiment, the kitcan include a compound or composition as described herein and a labelthat indicates that the contents are to be administered to a patientwith one or more of glioblastoma, ovarian, breast, pancreatic cancers,acute lymphoblastic leukemia, acute megakaryoblastic leukemia, chronicmyeloid leukemia, Alzheimer's Disease, Amyotrophic Lateral Sclerosis,CDKL5 Deficiency Disorder, Down Syndrome, Frontotemporal Dementia withParkinsonism-17 (FTDP-17), Lewy body dementia, Parkinson's Disease,Pick's Disease, Autism, Dementia, Epilepsy, Huntington's Disease, andMultiple Sclerosis.

Methods of Treatment

The compounds and compositions provided herein can be used as inhibitorsof DYRK1A, and thus can be used to treat a variety of disorders anddiseases in which over expression of DYRK1A is implicated, such ascancer and neurological conditions/disorders/diseases. Non-limitingexamples of diseases which can be treated with the compounds andcompositions provided herein include a variety of cancers, Alzheimer'sDisease, Amyotrophic Lateral Sclerosis, CDKL5 Deficiency Disorder, DownSyndrome, Frontotemporal Dementia with Parkinsonism-17 (FTDP-17), Lewybody dementia, Parkinson's Disease, Pick's Disease, and additionaldiseases with pronounced neurodegeneration such as Autism, Dementia,Epilepsy, Huntington's Disease, Multiple Sclerosis; diseases anddisorders associated with acquired brain injury such as ChronicTraumatic Encephalopathy, Traumatic Brain Injury, Tumor, Stroke,tauopathies (e.g., Pick's disease, progressive supranuclear palsy,corticobasal degeneration, argyrophilic grain disease, globular glialtauopathies, primary age-related tauopathy, which includesneurofibrillary tangle dementia, chronic traumatic encephalopathy (CTE),frontotemporal lobar degeneration with tau inclusions (FTLD-tau), andaging-related tau astrogliopathy. Clinical symptoms includefrontotemporal dementia, corticobasal syndrome, Richardson syndrome,parkinsonism, pure akinesia with gait freezing and, rarely, motor neuronsymptoms or cerebellar ataxia, diabetes, psoriasis, knee osteoarthritis,tendinopathy, human immunodeficiency virus type 1 (HIV-1), humancytomegalovirus (HCMV), hepatitis C virus (HCV), and herpes simplexvirus 1 (HSV-1).

The gene encoding DYRK1A is located on chromosome 21, within the Downsyndrome critical region (DSCR), the triploidy of which is responsiblefor most Down syndrome-associated deficiencies (FEBS Journal (2011),278, 246-256). There is considerable genetical and pharmacologicalevidence showing that the mere 1.5-fold overexpression of DYRK1A isresponsible for most cognitive deficits observed in Down syndromepatients (Pharmacology & Therapeutics (2019), 194, 199-221 and BrainScience (2018), 8(10), 187). Genetical normalization of DYRK1A levels orpharmacological inhibition of its catalytic activity restores cognitivefunctions. The development of pharmacological inhibitors of DYRK1A is amajor avenue for the treatment of cognitive deficits associated withDown syndrome.

DYRK1A and DYRK1B are utilized during human cytomegalovirus (HCMV)placental replication. Inhibition of DYRKs prevent replication ofvarious viruses, including hepatitis C virus (HCV), humancytomegalovirus (HCMV), human immunodeficiency virus type 1 (HIV-1), andherpes simplex virus 1 (HSV-1) (Journal of Virology (2020), 94(6) andPLoS ONE (2015), 10, e0144229).

There is a growing body of evidence showing that DYRK1A/1B inhibitorsinduce the proliferation of insulin-producing pancreatic β-cells, makingDYRK1A/1B kinases attractive therapeutic targets for β-cell regenerationfor both type 1 and type 2 diabetes mellitus and gestational diabetes(Nature Communications (2015), 6(8372); Diabetes (2016), 65(6),1660-1671; JCI Insight (2020), 5(1), e132594; Science TranslationalMedicine (2020), 12(530); International Journal of Molecular Sciences(2021), 22(16), 9083; and Journal of Medicinal Chemistry (2021), 64(6),2901-2922). Other forms of diabetes that may be treated with DYRKinhibitors are maturity onset diabetes of the young (MODY, monogenicdiabetes), cases of diabetes that are caused by the body's tissuereceptors not responding to insulin, double diabetes (when a type 1diabetic becomes insulin resistant), diabetes associated with excessivesecretion of insulin-antagonistic hormones, malnutrition-relateddiabetes mellitus (ICD-10 code E12), and diabetes caused by any geneticmutations (autosomal or mitochondrial) that leads to defects in betacell function.

There is abundant literature linking DYRK1A with solid cancers andleukemias (Pharmacology & Therapeutics (2015), 151, 87-98; Cancers(2020), 12(8), 2106; and Cellular and Molecular Life Sciences (2021),78, 603-619). The most prominent examples are pancreatic cancer (Gut(2019), 68(8), 1465-1476 and Gene (2020), 758, 144960), brain tumors,glioblastoma (Journal of Clinical Investigation (2013), 123(6),2475-2487), acute megakaryoblastic leukemia (AMKL) (Journal of ClinicalInvestigation (2012), 122(3), 948-962), and acute lymphoblastic leukemia(ALL) (Journal of Clinical Investigation (2021), 131(1), e135937). Othercancers linked to DYRK1A are ovarian (Frontiers in Oncology (2021), 11,637193), head and neck squamous cell carcinoma (Scientific Reports(2016), 6, 36132), hepatocellular carcinoma (Cell Death & Disease(2021), 12, 125), DYRK1A regulates DNA damage response (ScientificReports (2019), 9, 6014 and Scientific Reports (2019), 9, 6539). In somesituations, DYRK1A appears to function as a tumor-suppressor protein(Molecular & Cellular Oncology (2015), 2(1), e970048 and Nature (2016),529, 172-177).

Other cancers can also be treated with the compounds and compositionsdescribed herein.

More particularly, cancers that may be treated by the compounds,compositions and methods described herein include, but are not limitedto, the following:

1) Breast cancers, including, for example ER⁺ breast cancer, ER⁻ breastcancer, her2⁻ breast cancer, her2⁺ breast cancer, stromal tumors such asfibroadenomas, phyllodes tumors, and sarcomas, and epithelial tumorssuch as large duct papillomas; carcinomas of the breast including insitu (noninvasive) carcinoma that includes ductal carcinoma in situ(including Paget's disease) and lobular carcinoma in situ, and invasive(infiltrating) carcinoma including, but not limited to, invasive ductalcarcinoma, invasive lobular carcinoma, medullary carcinoma, colloid(mucinous) carcinoma, tubular carcinoma, and invasive papillarycarcinoma; chemoresistant breast cancers (TNBC), and miscellaneousmalignant neoplasms. Further examples of breast cancers can includeluminal A, luminal B, basal A, basal B, and triple negative breastcancer, which is estrogen receptor negative (ER⁻), progesterone receptornegative, and her2 negative (her2⁻). In some embodiments, the breastcancer may have a high risk Oncotype score.

2) Cardiac cancers, including, for example sarcoma, e.g., angiosarcoma,fibrosarcoma, rhabdomyosarcoma, and liposarcoma; myxoma; rhabdomyoma;fibroma; lipoma and teratoma.

3) Lung cancers, including, for example, bronchogenic carcinoma, e.g.,squamous cell, undifferentiated small cell, undifferentiated large cell,and adenocarcinoma; alveolar and bronchiolar carcinoma; bronchialadenoma; sarcoma; lymphoma; chondromatous hamartoma; chemoresistantsmall cell lung cancer (SCLC), and mesothelioma.

4) Gastrointestinal cancer, including, for example, cancers of theesophagus, e.g., squamous cell carcinoma, adenocarcinoma,leiomyosarcoma, and lymphoma; cancers of the stomach, e.g., carcinoma,lymphoma, and leiomyosarcoma; cancers of the pancreas, e.g., ductaladenocarcinoma, insulinoma, glucagonoma, gastrinoma, carcinoid tumors,and vipoma; colon cancers with APC gene mutations; cancers of the smallbowel, e.g., adenocarcinoma, lymphoma, carcinoid tumors, Kaposi'ssarcoma, leiomyoma, hemangioma, lipoma, neurofibroma, and fibroma;cancers of the large bowel, e.g., adenocarcinoma, tubular adenoma,villous adenoma, hamartoma, and leiomyoma.

5) Genitourinary tract cancers, including, for example, cancers of thekidney, e.g., adenocarcinoma, Wilm's tumor (nephroblastoma), lymphoma,and leukemia; cancers of the bladder and urethra, e.g., squamous cellcarcinoma, transitional cell carcinoma, and adenocarcinoma; cancers ofthe prostate, e.g., adenocarcinoma, and sarcoma; cancer of the testis,e.g., seminoma, teratoma, embryonal carcinoma, teratocarcinoma,choriocarcinoma, sarcoma, interstitial cell carcinoma, fibroma,fibroadenoma, adenomatoid tumors, and lipoma.

6) Liver cancers, including, for example, hepatoma, e.g., hepatocellularcarcinoma; cholangiocarcinoma; hepatoblastoma; angiosarcoma;hepatocellular adenoma; and hemangioma.

7) Bone cancers, including, for example, osteogenic sarcoma(osteosarcoma), fibrosarcoma, malignant fibrous histiocytoma,chondrosarcoma, Ewing's sarcoma, malignant lymphoma (reticulum cellsarcoma), multiple myeloma, malignant giant cell tumor chordoma,osteochrondroma (osteocartilaginous exostoses), benign chondroma,chondroblastoma, chondromyxofibroma, osteoid osteoma and giant celltumors.

8) Nervous system cancers, including, for example, cancers of the skull,e.g., osteoma, hemangioma, granuloma, xanthoma, and osteitis deformans;cancers of the meninges, e.g., meningioma, meningiosarcoma, andgliomatosis; cancers of the brain, e.g., astrocytoma, medulloblastoma,glioma, ependymoma, germinoma (pinealoma), glioblastoma multiform,oligodendroglioma, oligodendrocytoma, schwannoma, retinoblastoma, andcongenital tumors; and cancers of the spinal cord, e.g., neurofibroma,meningioma, glioma, and sarcoma.

9) Gynecological cancers, including, for example, cancers of the uterus,e.g., endometrial cancers (e.g., carcinoma, endometrioid adenocarcinoma,serous carcinoma, clear cell carcinoma, mucinous carcinomas, mixed orundifferentiated carcinoma (including mixed Mullerian tumor),endometrial stromal sarcoma, squamous cell carcinoma of the endometrium,urothelial carcinoma, endometrial cancer with CTNNB1 mutations); cancersof the cervix, e.g., cervical carcinoma, and pre tumor cervicaldysplasia; cancers of the ovaries, e.g., BRCA-mutant ovarian cancer,surface epithelial-stromal tumors (epithelial ovarian cancer (Type 1(endometroid, mucinous, clear cell, low grade serous) or Type 2 (poorlydifferentiated, carcinosarcoma, and high grade serous))), ovariancarcinoma, including serous cystadenocarcinoma, mucinouscystadenocarcinoma, endometrioid tumors, small cell ovarian cancer(small cell ovarian cancer of hypercalcemic type, small cell ovariancancer of pulmonary type) unclassified carcinoma, granulosa theca celltumors, Sertoli Leydig cell tumors, dysgerminoma, and malignantteratoma; cancers of the vulva, e.g., squamous cell carcinoma,intraepithelial carcinoma, adenocarcinoma, fibrosarcoma, and melanoma;cancers of the vagina, e.g., clear cell carcinoma, squamous cellcarcinoma, botryoid sarcoma, and embryonal rhabdomyosarcoma; and cancersof the fallopian tubes, e.g., carcinoma, primary fallopian tube cancer;Primary peritoneal cancer (also known as serous surface papillarycarcinoma, primary peritoneal carcinoma, extra-ovarian serous carcinoma,primary serous papillary carcinoma, and psammomacarcinoma).

10) Hematologic cancers, including, for example, cancers of the blood,e.g., acute myeloid leukemia, chronic myeloid leukemia, myelodysplasticsyndromes (refractory cytopenia with unilineage dysplasia (refractoryanemia, refractory neutropenia, and refractory thrombocytopenia),refractory anemia with ring sideroblasts, refractory cytopenia withmultilineage dysplasia, refractory anemias with excess blasts I and II,refractory cytopenia of childhood), and myeloproliferative neoplasms,acute lymphoblastic leukemia, chronic lymphocytic leukemia,myeloproliferative diseases, multiple myeloma, myelodysplastic syndrome,myelodysplastic-myeloproliferative diseases, Hodgkin's lymphoma,non-Hodgkin's lymphoma (malignant lymphoma) and Waldenström'smacroglobulinemia.

11) Skin cancers and skin disorders, including, for example, malignantmelanoma and metastatic melanoma, basal cell carcinoma, squamous cellcarcinoma, Kaposi's sarcoma, moles dysplastic nevi, lipoma, angioma,dermatofibroma, keloids, and scleroderma.

12) Adrenal gland cancers, including, for example, neuroblastoma.

13) Soft-tissue sarcomas (STS) such as fibrosarcoma, malignant fibroushistiocytoma, dermatofibrosarcoma, liposarcoma, rhabdomyosarcoma,leiomyosarcoma, hemangiosarcoma, Kaposi's sarcoma, lymphangiosarcoma,synovial sarcoma, malignant peripheral nerve sheath tumors (also calledneurofibrosarcomas, malignant schwannomas, and neurogenic sarcomas),neurofibrosarcoma, extraskeletal chondrosarcoma, extraskeletalosteosarcoma, extraskeletal myxoid chondrosarcoma, extraskeletalmesenchymal, embryonal, alveolar soft part sarcoma, and infantilehemangio-pericytoma.

More particularly, tumors of the central nervous system that may betreated by the compounds, compositions and methods described hereininclude:

1) Astrocytic tumors, e.g., diffuse astrocytoma (fibrillary,protoplasmic, gemistocytic, mixed), anaplastic (malignant) astrocytoma,glioblastoma multiforme (giant cell glioblastoma and gliosarcoma),pilocytic astrocytoma (pilomyxoid astrocytoma), pleomorphicxanthoastrocytoma, subependymal giant cell astrocytoma, and gliomatosiscerebri.

2) Oligodendroglial tumors, e.g., oligodendroglioma and anaplasticoligodendroglioma.

3) Oligoastrocytic tumors, e.g., oligoastrocytoma and anaplasticoligoastrocytoma.

4) Ependymal tumors, e.g., subependymoma, myxopapillary ependymoma,ependymoma, (cellular, papillary, clear cell, tanycytic), and anaplastic(malignant) ependymoma.

5) Choroid plexus tumors, e.g., choroid plexus papilloma, atypicalchoroid plexus papilloma, and choroid plexus carcinoma.

6) Neuronal and mixed neuronal-glial tumors, e.g., gangliocytoma,ganglioglioma, dysembryoplastic neuroepithelial tumor (DNET), dysplasticgangliocytoma of the cerebellum (Lhermitte-Duclos), desmoplasticinfantile astrocytoma/ganglioglioma, central neurocytoma, anaplasticganglioglioma, extraventricular neurocytoma, cerebellar liponeurocytoma,Papillary glioneuronal tumor, Rosette-forming glioneuronal tumor of thefourth ventricle, and paraganglioma of the filum terminale.

7) Pineal tumors, e.g., pineocytoma, pineoblastoma, papillary tumors ofthe pineal region, and pineal parenchymal tumor of intermediatedifferentiation.

8) Embryonal tumors, e.g., medulloblastoma (medulloblastoma withextensive nodularity, anaplastic medulloblastoma, desmoplastic, largecell, melanotic, medullomyoblastoma), medulloepithelioma, supratentorialprimitive neuroectodermal tumors, and primitive neuroectodermal tumors(PNETs) such as neuroblastoma, ganglioneuroblastoma, ependymoblastoma,and atypical teratoid/rhabdoid tumor.

9) Neuroblastic tumors, e.g., olfactory (esthesioneuroblastoma),olfactory neuroepithelioma, and neuroblastomas of the adrenal gland andsympathetic nervous system.

10) Glial tumors, e.g., astroblastoma, chordoid glioma of the thirdventricle, and angiocentric glioma.

11) Tumors of cranial and paraspinal nerves, e.g., schwannoma,neurofibroma Perineurioma, and malignant peripheral nerve sheath tumor.

12) Tumors of the meninges such as tumors of meningothelial cells, e.g.,meningioma (atypical meningioma and anaplastic meningioma); mesenchymaltumors, e.g., lipoma, angiolipoma, hibernoma, liposarcoma, solitaryfibrous tumor, fibrosarcoma, malignant fibrous histiocytoma, leiomyoma,leiomyosarcoma, rhabdomyoma, rhabdomyosarcoma, chondroma,chondrosarcoma, osteoma, osteosarcoma, osteochondroma, haemangioma,epithelioid hemangioendothelioma, haemangiopericytoma, anaplastichaemangiopericytoma, angiosarcoma, Kaposi Sarcoma, and Ewing Sarcoma;primary melanocytic lesions, e.g., diffuse melanocytosis, melanocytoma,malignant melanoma, meningeal melanomatosis; and hemangioblastomas.

13) Tumors of the hematopoietic system, e.g., malignant Lymphomas,plasmocytoma, and granulocytic sarcoma.

14) Germ cell tumors, e.g., germinoma, embryonal carcinoma, yolk sactumor, choriocarcinoma, teratoma, and mixed germ cell tumors.

15) Tumors of the sellar region, e.g., craniopharyngioma, granular celltumor, pituicytoma, and spindle cell oncocytoma of the adenohypophysis.

Cancers may be solid tumors that may or may not be metastatic. Cancersmay also occur, as in leukemia, as a diffuse tissue. Thus, the term“tumor cell,” as provided herein, includes a cell afflicted by any oneof the above identified disorders.

A method of treating cancer using a compound or composition as describedherein may be combined with existing methods of treating cancers, forexample by chemotherapy, irradiation, or surgery (e.g., oophorectomy).In some embodiments, a compound or composition can be administeredbefore, during, or after another anticancer agent or treatment.

There is mounting evidence for a role of DYRK1A in the onset ofAlzheimer's Disease (Future Medicinal Chemistry (2016), 8(6), 681-696and European Journal of Medicinal Chemistry (2018), 158, 559-592).DYRK1A phosphorylates key substrates involved in Alzheimer's Disease anddementia: Tau, septin 4, amyloid precursor protein (APP), presenilin 1,neprilysin, Munc18-1, α-synuclein, RCAN1, and β-tubulin. By modulatingalternative splicing of Tau exon 10, DYRK1A favors the production of the3R-Tau splice isoform (characteristic for DS/AD/tauopathy) over the4R-Tau isoform (Journal of Biological Chemistry (2015), 290,15219-15237).

Genome-wide association studies (GWAS) have revealed that DYRK1A is arisk factor for Parkinson's Disease (The Lancet Neurology (2019),18(12), 1091-1102). DYRK1A phosphorylates key factors for Parkinson'sDisease such as parkin, septin 4, and α-synuclein. Upregulation ofmicro-RNAs specific for Parkinson's Disease targets DYRK1A expression.There is further evidence that DYRK1A expression is increased inParkinson's Disease and in Pick's disease (Neurobiology of Disease(2005), 20(2), 392-400).

The compounds and compositions provided herein can be used as inhibitorsand/or modulators of the enzyme DYRK1A, and thus can be used to treat avariety of disorders and diseases associated with tau protein,including, but not limited to, Alzheimer's disease, amyotrophic lateralsclerosis (ALS), down syndrome, frontotemporal dementia (FTD) includingFTD with Parkinsonism-17 (FTDP-17), behavioural variant frontotemporaldementia (bvFTD), FTD in patients with motor neuron disease (MND)(typically amyotrophic lateral sclerosis, also called FTD-ALS),corticobasal degeneration (CBD) (also called corticobasal ganglionicdegeneration), progressive supranuclear palsy, primary progressiveaphasia (PPA), globular glial tauopathy (GGT), myotonic dystrophy type 1(DM1) (also called Steinert disease), myotonic dystrophy type 2 (DM2)(also called proximal myotonic myopathy), Guam complex, argyrophilicgrain disease, dementia pugilistica, post-encephalitic parkinsonism,Lewy body dementia, Parkinson's disease, Pick's disease, and additionaldiseases with pronounced neurodegeneration such as autism, dementia,epilepsy, Huntington's disease, multiple sclerosis; diseases anddisorders associated with acquired brain injury such as chronictraumatic encephalopathy, traumatic brain injury, tumor, and stroke.

Non-limiting examples of neurological disorders (e.g., neurologicalconditions and neurological diseases) which can be treated with thecompounds and compositions provided herein include Alzheimer's disease,aphasia, apraxia, arachnoiditis, ataxia telangiectasia, attentiondeficit hyperactivity disorder, auditory processing disorder, autism,alcoholism, Bell's palsy, bipolar disorder, brachial plexus injury,Canavan disease, carpal tunnel syndrome, causalgia, central painsyndrome, central pontine myelinolysis, centronuclear myopathy, cephalicdisorder, cerebral aneurysm, cerebral arteriosclerosis, cerebralatrophy, cerebral gigantism, cerebral palsy, cerebral vasculitis,cervical spinal stenosis, Charcot-Marie-Tooth disease, Chiarimalformation, chronic fatigue syndrome, chronic inflammatorydemyelinating polyneuropathy (CIDP), chronic pain, Coffin-Lowrysyndrome, complex regional pain syndrome, compression neuropathy,congenital facial diplegia, corticobasal degeneration, cranialarteritis, craniosynostosis, Creutzfeldt-Jakob disease, cumulativetrauma disorder, Cushing's syndrome, cytomegalic inclusion body disease(CIBD), Dandy-Walker syndrome, Dawson disease, De Morsier's syndrome,Dejerine-Klumpke palsy, Dejerine-Sottas disease, delayed sleep phasesyndrome, dementia, dermatomyositis, developmental dyspraxia, diabeticneuropathy, diffuse sclerosis, Dravet syndrome, dysautonomia,dyscalculia, dysgraphia, dyslexia, dystonia, empty sella syndrome,encephalitis, encephalocele, encephalotrigeminal angiomatosis,encopresis, epilepsy, Erb's palsy, erythromelalgia, essential tremor,Fabry's disease, Fahr's syndrome, familial spastic paralysis, febrileseizure, Fisher syndrome, Friedreich's ataxia, fibromyalgia, Foville'ssyndrome, Gaucher's disease, Gerstmann's syndrome, giant cell arteritis,giant cell inclusion disease, globoid cell leukodystrophy, gray matterheterotopia, Guillain-Barré syndrome, HTLV-1 associated myelopathy,Hallervorden-Spatz disease, hemifacial spasm, hereditary spasticparaplegia, heredopathia atactica polyneuritiformis, herpes zosteroticus, herpes zoster, Hirayama syndrome, holoprosencephaly,Huntington's disease, hydranencephaly, hydrocephalus, hypercortisolism,hypoxia, immune-mediated encephalomyelitis, inclusion body myositis,incontinentia pigmenti, infantile phytanic acid storage disease,infantile Refsum disease, infantile spasms, inflammatory myopathy,intracranial cyst, intracranial hypertension, Joubert syndrome, Karaksyndrome, Kearns-Sayre syndrome, Kennedy disease, Kinsbourne syndrome,Klippel Feil syndrome, Krabbe disease, Kugelberg-Welander disease, kuru,Lafora disease, Lambert-Eaton myasthenic syndrome, Landau-Kleffnersyndrome, lateral medullary (Wallenberg) syndrome, Leigh's disease,Lennox-Gastaut syndrome, Lesch-Nyhan syndrome, leukodystrophy, Lewy bodydementia, lissencephaly, locked-in syndrome, Lou Gehrig's disease,lumbar disc disease, lumbar spinal stenosis, Lyme disease,Machado-Joseph disease (Spinocerebellar ataxia type 3), macrencephaly,macropsia, megalencephaly, Melkersson-Rosenthal syndrome, Meniere'sdisease, meningitis, Menkes disease, metachromatic leukodystrophy,microcephaly, micropsia, Miller Fisher syndrome, misophonia,mitochondrial myopathy, Mobius syndrome, monomelic amyotrophy, motorneuron disease, motor skills disorder, Moyamoya disease,mucopolysaccharidoses, multi-infarct dementia, multifocal motorneuropathy, multiple sclerosis, multiple system atrophy, musculardystrophy, myalgic encephalomyelitis, myasthenia gravis, myelinoclasticdiffuse sclerosis, myoclonic Encephalopathy of infants, myoclonus,myopathy, myotubular myopathy, myotonia congenital, narcolepsy,neurofibromatosis, neuroleptic malignant syndrome, lupus erythematosus,neuromyotonia, neuronal ceroid lipofuscinosis, Niemann-Pick disease,O'Sullivan-McLeod syndrome, occipital Neuralgia, occult SpinalDysraphism Sequence, Ohtahara syndrome, olivopontocerebellar atrophy,opsoclonus myoclonus syndrome, optic neuritis, orthostatic hypotension,palinopsia, paresthesia, Parkinson's disease, paramyotonia Congenita,paraneoplastic diseases, paroxysmal attacks, Parry-Romberg syndrome,Pelizaeus-Merzbacher disease, periodic paralyses, peripheral neuropathy,photic sneeze reflex, phytanic acid storage disease, Pick's disease,polymicrogyria (PMG), polymyositis, porencephaly, post-polio syndrome,postherpetic neuralgia (PHN), postural hypotension, Prader-Willisyndrome, primary lateral sclerosis, prion diseases, progressivehemifacial atrophy, progressive multifocal leukoencephalopathy,progressive supranuclear palsy, pseudotumor cerebri, Ramsay Huntsyndrome type I, Ramsay Hunt syndrome type II, Ramsay Hunt syndrome typeIII, Rasmussen's encephalitis, reflex neurovascular dystrophy, Refsumdisease, restless legs syndrome, retrovirus-associated myelopathy, Rettsyndrome, Reye's syndrome, rhythmic movement disorder, Romberg syndrome,Saint Vitus dance, Sandhoff disease, schizophrenia, Schilder's disease,schizencephaly, sensory integration dysfunction, septo-optic dysplasia,Shy-Drager syndrome, Sjögren's syndrome, snatiation, Sotos syndrome,spasticity, spina bifida, spinal cord tumors, spinal muscular atrophy,spinocerebellar ataxia, Steele-Richardson-Olszewski syndrome,Stiff-person syndrome, stroke, Sturge-Weber syndrome, subacutesclerosing panencephalitis, subcortical arteriosclerotic encephalopathy,superficial siderosis, Sydenham's chorea, syncope, synesthesia,syringomyelia, tarsal tunnel syndrome, tardive dyskinesia, tardivedysphrenia, Tarlov cyst, Tay-Sachs disease, temporal arteritis, tetanus,tethered spinal cord syndrome, Thomsen disease, thoracic outletsyndrome, tic douloureux, Todd's paralysis, Tourette syndrome, toxicencephalopathy, transient ischemic attack, transmissible spongiformencephalopathies, transverse myelitis, tremor, trigeminal neuralgia,tropical spastic paraparesis, trypanosomiasis, tuberous sclerosis,ubisiosis, Von Hippel-Lindau disease (VHL), Viliuisk Encephalomyelitis(VE), Wallenberg's syndrome, Werdnig, Hoffman disease, west syndrome,Williams syndrome, Wilson's disease, and Zellweger syndrome.

The compounds and compositions may also be useful in the inhibition ofthe development of invasive cancer, tumor angiogenesis and metastasis.

In some embodiments, the pharmaceutical composition comprises atherapeutically effective amount of a compound of Formulas I, Ia, Ib,Ic, Id, and Ie, or a pharmaceutically acceptable salt thereof, and apharmaceutically acceptable excipient.

In some embodiments, the disorder or disease is cancer.

In some embodiments, the disorder or disease is metastatic melanoma.

In some embodiments, the disorder or disease is tendon regeneration.

In some embodiments, the disorder or disease is diabetes.

In some embodiments, the disorder or disease is degenerative discdisease.

In some embodiments, the disorder or disease is osteoarthritis.

In some embodiments, the disorder or disease is a viral infection.

In some embodiments, the disorder or disease is a neurological disorder.

In some embodiments, the disorder or disease is Alzheimer's disease.

In some embodiments, the disorder or disease is osteoarthritis.

In some embodiments, the patient is a human.

In some embodiments, the cancer is chosen from: hepatocellularcarcinoma, colon cancer, breast cancer, pancreatic cancer, chronicmyeloid leukemia (CML), chronic myelomonocytic leukemia, chroniclymphocytic leukemia (CLL), acute myeloid leukemia, acute lymphocyticleukemia, Hodgkin lymphoma, lymphoma, sarcoma, and ovarian cancer.

In some embodiments, the cancer is chosen from: lung cancer—non-smallcell, lung cancer—small cell, multiple myeloma, nasopharyngeal cancer,neuroblastoma, osteosarcoma, penile cancer, pituitary tumors, prostatecancer, retinoblastoma, synovial sarcoma, rhabdomyosarcoma, salivarygland cancer, skin cancer—basal and squamous cell, skin cancer—melanoma,small intestine cancer, stomach (gastric) cancers, testicular cancer,thymus cancer, thyroid cancer, uterine sarcoma, vaginal cancer, vulvarcancer, laryngeal or hypopharyngeal cancer, kidney cancer, Kaposisarcoma, gestational trophoblastic disease, gastrointestinal stromaltumor, gastrointestinal carcinoid tumor, gallbladder cancer, eye cancer(melanoma and lymphoma), Ewing tumor, esophagus cancer, endometrialcancer, colorectal cancer, cervical cancer, brain or spinal cord tumor,bone metastasis, bone cancer, bladder cancer, bile duct cancer, analcancer and adrenal cortical cancer.

In some embodiments, the cancer is hepatocellular carcinoma; in someembodiments, the cancer is colon cancer; in some embodiments, the canceris colorectal cancer; in some embodiments, the cancer is breast cancer;in some embodiments, the cancer is pancreatic cancer; in someembodiments, the cancer is chronic myeloid leukemia (CML); in someembodiments, the cancer is chronic myelomonocytic leukemia; in someembodiments, the cancer is chronic lymphocytic leukemia (CLL); in someembodiments, the cancer is acute myeloid leukemia; in some embodiments,the cancer is acute lymphocytic leukemia; in some embodiments, thecancer is Hodgkin lymphoma; in some embodiments, the cancer is lymphoma;in some embodiments, the cancer is sarcoma; in some embodiments, thecancer is ovarian cancer; in some embodiments, the cancer is lungcancer—non-small cell; in some embodiments, the cancer is lungcancer—small cell; in some embodiments, the cancer is multiple myeloma;in some embodiments, the cancer is nasopharyngeal cancer; in someembodiments, the cancer is neuroblastoma; in some embodiments, thecancer is osteosarcoma; in some embodiments, the cancer is penilecancer; in some embodiments, the cancer is pituitary tumors; in someembodiments, the cancer is prostate cancer; in some embodiments, thecancer is retinoblastoma; in some embodiments, the cancer isrhabdomyosarcoma; in some embodiments, the cancer is salivary glandcancer; in some embodiments, the cancer is skin cancer—basal andsquamous cell; in some embodiments, the cancer is skin cancer—melanoma;in some embodiments, the cancer is small intestine cancer; in someembodiments, the cancer is stomach (gastric) cancers; in someembodiments, the cancer is testicular cancer; in some embodiments, thecancer is thymus cancer; in some embodiments, the cancer is thyroidcancer; in some embodiments, the cancer is uterine sarcoma; in someembodiments, the cancer is vaginal cancer; in some embodiments, thecancer is vulvar cancer; in some embodiments, the cancer is Wilms tumor;in some embodiments, the cancer is laryngeal or hypopharyngeal cancer;in some embodiments, the cancer is kidney cancer; in some embodiments,the cancer is Kaposi sarcoma; in some embodiments, the cancer isgestational trophoblastic disease; in some embodiments, the cancer isgastrointestinal stromal tumor; in some embodiments, the cancer isgastrointestinal carcinoid tumor; in some embodiments, the cancer isgallbladder cancer; in some embodiments, the cancer is eye cancer(melanoma and lymphoma); in some embodiments, the cancer is Ewing tumor;in some embodiments, the cancer is esophagus cancer; in someembodiments, the cancer is endometrial cancer; in some embodiments, thecancer is colorectal cancer; in some embodiments, the cancer is cervicalcancer; in some embodiments, the cancer is brain or spinal cord tumor;in some embodiments, the cancer is bone metastasis; in some embodiments,the cancer is bone cancer; in some embodiments, the cancer is bladdercancer; in some embodiments, the cancer is bile duct cancer; in someembodiments, the cancer is anal cancer; and in some embodiments, thecancer is adrenal cortical cancer.

In some embodiments, the cancer is the cancer is selected from the groupconsisting of: brain tumors, glioblastoma, ovarian, breast, head andneck squamous cell carcinoma, hepatocellular carcinoma, pancreaticcancer, acute lymphoblastic leukemia, acute megakaryoblastic leukemia,and chronic myeloid leukemia.

In some embodiments, the disorder or disease is a neurologicalcondition, disorder, or disease, wherein the neurological disease isselected from: Alzheimer's disease, frontotemporal dementias,Parkinson's disease, Huntington's disease, progressive supranuclearpalsy, corticobasal degeneration, multiple system atrophy, amyotrophiclateral sclerosis (ALS), inclusion body myositis, autism, degenerativemyopathies.

In some embodiments, the disorder or disease is selected from the groupconsisting of: Alzheimer's Disease, Amyotrophic Lateral Sclerosis, DownSyndrome, Frontotemporal Dementia with Parkinsonism-17 (FTDP-17), Lewybody dementia, Parkinson's Disease, Pick's Disease, and additionaldiseases with pronounced neurodegeneration such as Autism, Dementia,Epilepsy, Huntington's Disease, Multiple Sclerosis; diseases anddisorders associated with acquired brain injury such as ChronicTraumatic Encephalopathy, Traumatic Brain Injury, Tumor, and Stroke.

In some embodiments, the disorder or disease is a neurological disorder,wherein the neurological disorder is selected from the group consistingof: Alzheimer's Disease, Amyotrophic Lateral Sclerosis, CDKL5 DeficiencyDisorder, Down Syndrome, Frontotemporal Dementia with Parkinsonism-17(FTDP-17), Lewy body dementia, Parkinson's Disease, Pick's Disease, andadditional diseases with pronounced neurodegeneration such as Autism,Dementia, Epilepsy, Huntington's Disease, Multiple Sclerosis; diseasesand disorders associated with acquired brain injury such as ChronicTraumatic Encephalopathy, Traumatic Brain Injury, Tumor, Stroke, Pickdisease, progressive supranuclear palsy, corticobasal degeneration,argyrophilic grain disease, globular glial tauopathies, primaryage-related tauopathy, neurofibrillary tangle dementia, chronictraumatic encephalopathy (CTE), frontotemporal lobar degeneration withtau inclusions (FTLD-tau), and aging-related tau astrogliopathy.

In some embodiments, the disorder or disease is Alzheimer's disease.

In some embodiments, a compound of Formulas I, Ia, Ib, Ic, Id, and Ieinhibits DYRK1A.

In some embodiments, the method treats a disease or disorder mediated bykinase activity in a patient, the method comprises administering to thepatient a therapeutically effective amount of a compound (or compounds)of Formulas I, Ia, Ib, Ic, Id, and Ie, or a pharmaceutically acceptablesalt thereof.

In some embodiments, the disease or disorder comprises tumor growth,cell proliferation, or angiogenesis.

In some embodiments, the method inhibits the activity of a proteinkinase receptor, the method comprises contacting the receptor with aneffective amount of a compound (or compounds) of Formulas I, Ia, Ib, Ic,Id, and Ie, or a pharmaceutically acceptable salt thereof.

In some embodiments, the method treats a disease or disorder associatedwith aberrant cellular proliferation in a patient; the method comprisesadministering to the patient a therapeutically effective amount of acompound (or compounds) of Formulas I, Ia, Ib, Ic, Id, and Ie, or apharmaceutically acceptable salt thereof.

In some embodiments, the method prevents or reduces abnormal cellularproliferation in a patient; the method comprises administering to thepatient a therapeutically effective amount of a compound (or compounds)of Formulas I, Ia, Ib, Ic, Id, and Ie, or a pharmaceutically acceptablesalt thereof.

In some embodiments, the method treats a disease or disorder associatedwith aberrant cellular proliferation in a patient, the method comprisesadministering to the patient a pharmaceutical composition comprising oneor more of the compounds of claim 1 in combination with apharmaceutically acceptable carrier and one or more other agents.

Evaluation of Biological Activity

The biological activity of the compounds described herein can be testedusing any suitable assay known to those of skill in the art. Forexample, the activity of a compound may be tested using one or more ofthe test methods outlined below.

For example, in vitro assays for DYRK1A biological activity may be used,e.g., regulation of microtubule-associated protein tau (MAPT/Tau)phosphorylation in neuronal cell lines such as the human SH-SY5Yneuroblastoma cell line. Assays for DYRK1A-regulated level ofphosphorylation can include monitoring levels of basal pSer396 Tau,which can be measured, for example, by serial dilutions of a candidateinhibitor composition using a ten micromolar top concentration anddetected by ELISA or Western Blotting. An exemplary assay forDYRK-1A-regulated phosphorylation uses the SH-SY5Y cells cultured in a96 well plate format for a period of time sufficient to stabilizemicrotubules and Tau phosphorylation, usually at least 2 days, thentreated with a ⅓ serial dilution of compounds overnight and lysed. Thecell lysate is resolved by SDS PAGE, then transferred to nitrocelluloseand probed with an antibody specific for pSer396 Tau. Thechemiluminescence signal for HRP-linked antibodies used in westernblotting is detected using a Carestream Image Station and blotdensitometry for pSer396 and beta-actin are analyzed using ImageJ (NIH).

In a further example, the activity of a candidate compound can bemeasured by phosphoTau (Thr212) AlphaLISA by adding the lysate mentionedabove onto total Tau-coated plates and detected with a specificpThr212Tau antibody. Colorimetric detection of AlphaLISA signal isperformed by EnVision Multilabel Plate Reader (Perkin Elmer).

To further illustrate this disclosure, the following examples areincluded. The examples should not, of course, be construed asspecifically limiting the disclosure. Variations of these exampleswithin the scope of the claims are within the purview of one skilled inthe art and are considered to fall within the scope of the disclosure asdescribed and claimed herein. The reader will recognize that the skilledartisan, armed with the present disclosure, and skill in the art is ableto prepare and use the disclosure without exhaustive examples.

EXAMPLES Compound Preparation

The starting materials used in preparing the compounds of the disclosureare known, made by known methods, or are commercially available. It willbe apparent to the skilled artisan that methods for preparing precursorsand functionality related to the compounds claimed herein are generallydescribed in the literature. The skilled artisan given the literatureand this disclosure is well equipped to prepare any of the compounds.

It is recognized that the skilled artisan in the art of organicchemistry can readily carry out manipulations without further direction,that is, it is well within the scope and practice of the skilled artisanto carry out these manipulations. These include reduction of carbonylcompounds to their corresponding alcohols, oxidations, acylations,aromatic substitutions, both electrophilic and nucleophilic,etherifications, esterification and saponification and the like. Thesemanipulations are discussed in standard texts such as March's AdvancedOrganic Chemistry: Reactions, Mechanisms, and Structure 7^(th) Ed., JohnWiley & Sons (2013), Carey and Sundberg, Advanced Organic Chemistry5^(th) Ed., Springer (2007), Comprehensive Organic Transformations: AGuide to Functional Group Transformations, 2^(nd) Ed., John Wiley & Sons(1999) (incorporated herein by reference in its entirety)and the like.

The skilled artisan will readily appreciate that certain reactions arebest carried out when other functionality is masked or protected in themolecule, thus avoiding any undesirable side reactions and/or increasingthe yield of the reaction. Often the skilled artisan utilizes protectinggroups to accomplish such increased yields or to avoid the undesiredreactions. These reactions are found in the literature and are also wellwithin the scope of the skilled artisan. Examples of many of thesemanipulations can be found for example in P. Wuts Greene's ProtectiveGroups in Organic Synthesis, 5th Ed., John Wiley & Sons (2014),incorporated herein by reference in its entirety.

Trademarks used herein are examples only and reflect illustrativematerials used at the time of the disclosure. The skilled artisan willrecognize that variations in lot, manufacturing processes, and the like,are expected. Hence the examples, and the trademarks used in them arenon-limiting, and they are not intended to be limiting, but are merelyan illustration of how a skilled artisan may choose to perform one ormore of the embodiments of the disclosure.

(¹H) nuclear magnetic resonance spectra (NMR) were measured in theindicated solvents on a Bruker NMR spectrometer (Avance TM DRX300, 300MHz for ¹H or Avance TM DRX500, 500 MHz for ¹H) or Varian NMRspectrometer (Mercury 400BB, 400 MHz for ¹H). Peak positions areexpressed in parts per million (ppm) downfield from tetramethylsilane.The peak multiplicities are denoted as follows, s, singlet; d, doublet;t, triplet; q, quartet; ABq, AB quartet; quin, quintet; sex, sextet;sep, septet; non, nonet; dd, doublet of doublets; ddd, doublet ofdoublets of doublets; d/ABq, doublet of AB quartet; dt, doublet oftriplets; td, triplet of doublets; dq, doublet of quartets; m,multiplet.

The following abbreviations have the indicated meanings:

Ac₂O=acetic anhydride

BrettPhos=2-(dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl

BrettPhos PdG3=[(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II)methanesulfonate methanesulfonate

brine=saturated aqueous sodium chloride

CDCl₃=deuterated chloroform

DCE=dichloroethane

DCM=dichloromethane

DIPEA=N,N-diisopropylethylamine

DMA=dimethylacetamide

DMAP=4-dimethylaminopyridine

DME=dimethoxyethane

DMF=N,N-dimethylformamide

DMSO-d₆=deuterated dimethylsulfoxide

ESIMS=electron spray mass spectrometry

EtOAc=ethyl acetate

HATU=1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium3-oxid hexafluorophosphate

HCl=hydrochloric acid

HOAc=acetic acid

IPA=isopropyl alcohol

ISCO=Teledyne ISCO, Inc brand CombiFlash® Rf 200

KOAc=potassium acetate

LAH=Lithium aluminum hydride

LC/MS=Liquid chromatography-mass spectrometry

=lithium bis(trimethylsilyl)amide

MeCN=acetonitrile

MeOH=methanol

MgSO₄=magnesium sulfate

MsCl=mesyl chloride or methanesulfonyl chloride

MTBE=methyl tert-butyl ether

MW=microwave irradiation

NaBH₃CN=sodium cyanoborohydride

NaHCO₃=sodium bicarbonate

NaBH(OAc)₃=Sodium triacetoxyborohydride

NMR=nuclear magnetic resonance

ON=overnight

Pd₂(dba)₃=tris(dibenzylideneacetone)dipalladium(0)

Pd(dppf)Cl₂=1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride

Pd(PPh₃)₄=tetrakis(triphenylphosphine)palladium(0)

PPTS=pyridinium p-toluenesulfonate

r.t.=room temperature

SPhos PdG3=[(2-Di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II)methanesulfonate

SPhos PdG4=Methanesulfonato(2-dicyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)(2′-methylamino-1,1′-biphenyl-2-yl)palladium(II)

TBAF=Tetra-n-butylammonium fluoride,

TEA=triethylamine

TFA=trifluoroacetic acid

THF=tetrahydrofuran

TLC=thin layer chromatography

X-PHOS=2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

The following example schemes are provided for the guidance of thereader, and collectively represent an example method for making thecompounds provided herein. Furthermore, other methods for preparingcompounds of the disclosure will be readily apparent to the person ofordinary skill in the art in light of the following reaction schemes andexamples. The skilled artisan is thoroughly equipped to prepare thesecompounds by those methods given the literature and this disclosure. Thecompound numberings used in the synthetic schemes depicted below aremeant for those specific schemes only, and should not be construed as orconfused with same numberings in other sections of the application.Unless otherwise indicated, all variables are as defined above.

General Procedures

Compounds of Formulas I and Ia of the present disclosure can be preparedas depicted in Scheme 1.

Scheme 1 describes a method for preparation of 1H-pyrrolo[2,3-b]pyridinederivatives (IV) by first reacting the boronic acid pinacol ester (I)using Suzuki coupling with a variety of bromines (II) to produceprotected 1H-pyrrolo[2,3-b]pyridine III. Deprotection of thephenylsulfonyl protected N with Cs₂CO₃ produces the final R¹ substituted1H-pyrrolo[2,3-b]pyridine IV.

In some embodiments, compounds of Formulas I, Ib, and Ic of the presentdisclosure can be prepared as depicted in Scheme 2.

Scheme 2 describes a method for preparation of R² substituted1H-pyrrolo[2,3-b]pyridine derivatives (XII) and (XV) by first protectingthe pyrrolo N of compound V with tosyl chloride to form VII. Suzukicoupling of the iodo (VII) with various boronic acid pinacol esters(VIII) yield derivatives IX. The halide on compound IX can be reactedwith various boronic acid pinacol esters (X) produces protectedcompounds (XI) which after deprotection yields 1H-pyrrolo[2,3-b]pyridinederivatives (XII). Alternatively, the halide on compound IX can becoupled with a variety of amines (XIII) to give derivatives (XIV) whichafter deprotection yields 1H-pyrrolo[2,3-b]pyridine derivatives (XV).

In other embodiments, compounds of Formulas I and Ie of the presentdisclosure can be prepared as depicted in Scheme 3.

Scheme 3 describes a method for preparation of R³ substituted1H-pyrrolo[2,3-b]pyridine derivatives (XXI) by first protecting thepyrrolo N of compound XVI with tosyl chloride to form XVII. Suzukicoupling of bromine (XVII) with various boronic acid pinacol esters(VIII) yields derivatives XVIII. The ester is hydrolyzed using NaOHwhich also removes the tosylate to give acid XIX. The acid is thencoupled with a variety of amines to produce R³ substituted1H-pyrrolo[2,3-b]pyridine derivatives (XXI).

In other embodiments, compounds of Formulas I and Ie of the presentdisclosure can be prepared as depicted in Scheme 4.

Scheme 4 describes a method for preparation of additional R³ substituted1H-pyrrolo[2,3-b]pyridine derivatives (XXVI) and (XXIX) by firstreacting the iodo compound (XXII) using Suzuki coupling with a varietyof boronic acid pinacol esters (VIII) to produce protected1H-pyrrolo[2,3-b]pyridine XIII. The halide of compound XIII can becoupled with a variety of primary amides (XXIV) to give derivative XXVwhich after deprotection yields R³ substituted 1H-pyrrolo[2,3-b]pyridinederivatives (XXVI). Alternatively, the halide on compound XIII can becoupled with a variety of boronic acid pinacol esters (XXVII) to givederivatives (XXVIII) which after deprotection yields R³ substituted1H-pyrrolo[2,3-b]pyridine derivatives (XXIX).

In other embodiments, compounds of Formulas I, Ib, and Id of the presentdisclosure can be prepared as depicted in Scheme 5.

Scheme 5 describes a method for preparation of additional R⁴ substituted1H-pyrrolo[2,3-b]pyridine derivatives (XXXIV), (XXXVII), (XL), and(XLIII) by first reacting the bromine compound (XXX) using Suzukicoupling with a variety of boronic acid pinacol esters (VIII) to produceprotected 1H-pyrrolo[2,3-b]pyridine XXXI. Negishi coupling of thechloride with a variety of organozinc compounds (XXXII) producederivative XXV which after deprotection yields R⁴ substituted1H-pyrrolo[2,3-b]pyridine derivatives (XXXIV). Alternatively, the halideon compound XXXI can be coupled with a variety of primary amides (XXXV)to give derivative XXXVI which after deprotection yields the R⁴substituted 1H-pyrrolo[2,3-b]pyridine derivatives (XXXVII). A thirdroute couples the halide (XXXI) with a variety of amines to producederivative (XXXIX) which after deprotection yields the R⁴ substituted1H-pyrrolo[2,3-b]pyridine derivatives (XL). A fourth route couples thehalide (XXXI) with a variety of various boronic acid pinacol esters(XLI) to produce derivative (XLII) which after deprotection gives the R⁴substituted 1H-pyrrolo[2,3-b]pyridine derivatives (XLIII).

Illustrative Compound Examples

Preparation of intermediate6-(difluoromethoxy)-3-iodo-1H-pyrrolo[2,3-b]pyridine (XLVI) is depictedbelow in Scheme 6.

Step 1

To a stirred suspension of 1,7-dihydropyrrolo[2,3-b]pyridin-6-one (XVIV)(commercially available from AstaTech Inc.) (0.5 g, 3.73 mmol) and2,2-difluoro-2-(fluorosulfonyl)acetic acid (commercially available fromAK Scientific, Inc.) (0.46 mL, 4.5 mmol) in MeCN (10 mL) was added underN₂, Na₂CO₃ (1.01 g, 9.32 mmol) (exothermic!). The mixture was stirred atroom temperature overnight. The reaction mixture was added to asaturated aqueous NaHCO₃ solution and extracted with CHCl₃. The organiclayer was separated, washed with water and brine. The crude product waspurified by ISCO (0→40% EtOAc/hexanes) to obtain6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridine (XLV) (442 mg, 2.400 mmol,64.4% yield) as a white solid. ESIMS found for C₈H₆F₂N₂O m/z 185.0(M+H).

Step 2

To a stirred solution of 6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridine(XLV) (0.4 g, 2.17 mmol) in DMF (6 mL) was portion-wise addedN-iodosuccinimide (0.49 g, 2.18 mmol) at 0° C. The reaction mixture wasstirred at room temperature for 2 h. The reaction mixture was pouredinto water (75 mL), stirred for 1 h and the solids were collected byfiltration, washed with water, and air-dried under vacuo overnight toobtain 6-(difluoromethoxy)-3-iodo-1H-pyrrolo[2,3-b]pyridine (XLVI) (631mg, 2.035 mmol, 93.7% yield) as a beige solid which is used for nextstep without purification. ESIMS found for C₈H₅F₂IN₂O m/z 310.9 (M+H).

Preparation of intermediate 6-ethoxy-3-iodo-1H-pyrrolo[2,3-b]pyridine(XLVIII) is depicted below in Scheme 7.

Step 1

A mixture of 1H-pyrrolo[2,3-b]pyridin-6-ol (XLIV) (commerciallyavailable from Advanced ChemBlocks Inc.) (2.03 g, 15.13 mmol), K₂CO₃(6.3 g, 45.58 mmol) and iodoethane (1.3 mL, 16.17 mmol) in acetone (30mL) was refluxed at 60° C. for 12 h. The reaction mixture was cooled,filtered through celite®, and washed with EtOAc. The filtrate wasconcentrated, and the residue was purified by column chromatography(0→5% MeOH/CHCl₃) to obtain 6-ethoxy-1H-pyrrolo[2,3-b]pyridine (XLVII)(1.44 g, 8.879 mmol, 58.7% yield) as a brown solid. ESIMS found forC₉H₁₀N₂O m/z 163.1 (M+H).

Step 2

To a stirred suspension of 6-ethoxy-1H-pyrrolo[2,3-b]pyridine (XLVII)(1.44 g, 8.88 mmol) in DMF (20 mL) was added portion wise1-iodopyrrolidine-2,5-dione (2 g, 8.89 mmol) and the mixture was stirredat room temperature for 0.5 h. LC/MS of the mixture showed 95% of theconversion. Another 0.05 equivalents of NIS was added, and the mixturewas stirred for another 30 minutes. LC/MS showed complete conversion.The reaction mixture was added to saturated aqueous NaHCO₃ (50 mL),stirred for 30 minutes and the resulting solids were collected byfiltration and dried to obtain 6-ethoxy-3-iodo-1H-pyrrolo[2,3-b]pyridine(XLVIII) (2.134 g, 7.407 mmol, 83.4% yield) as a beige solid. ESIMSfound for C₉H₉IN₂O m/z 288.9 (M+H).

The following intermediate was prepared in accordance with the proceduredescribed in the above Scheme 7.

6-(Cyclopropylmethoxy)-3-iodo-1H-pyrrolo[2,3-b]pyridine (XLIX): Beigesolid (396 mg, 1.261 mmol, 93.8% yield). ¹ESIMS found for C₁₁H₁₁IN₂O m/z314.95 (M+H).

Preparation of intermediate6-bromo-N-(1-methylpiperidin-4-yl)pyrazin-2-amine (LII) is depictedbelow in Scheme 8.

Step 1

A mixture of 2,6-dibromopyrazine (L) (2.38 g, 9.98 mmol), Cs₂CO₃ (6.51g, 19.97 mmol) and 4-amino-1-methylpiperidine (LI) (1.25 g, 10.98 mmol)in DMF (15 mL) was heated in a microwave at 100° C. for 0.6 h. Themixture was worked up with EtOAc-brine extraction. the product waspurified by silica column (0→20% 7 N NH₃ in MeOH/CHCl₃) to yield6-bromo-N-(1-methylpiperidin-4-yl)pyrazin-2-amine (LII) (1.06 g, 3.909mmol, 39.2% yield) as a yellow wax. ESIMS found for C₁₀H₁₅BrN₄ m/z 272.1(M+H).

Preparation of intermediate6-bromo-8-fluoro-2-methylimidazo[1,2-a]pyridine (LV) is depicted belowin Scheme 9.

Step 1

A mixture of 5-bromo-3-fluoropyridin-2-amine (LIII) (2.g, 10.47 mmol),1-bromo-2,2-dimethoxypropane (LIV) (2.11g, 11.53 mmol) and PPTS (0.26 g,1.05 mmol) in IPA (25 mL) was heated to 80° C. overnight. The reactionmixture was cooled to room temperature, added to water (200 mL) andstirred for 1 h. The resulting solids were collected and dried underhigh vacuo to obtain 6-bromo-8-fluoro-2-methylimidazo[1,2-a]pyridine(LV) (2.61 g, 11.40 mmol, 108.8% yield) as beige solid which was usedfor the next step without further purification. ESIMS found forC₈H₆BrFN₂ m/z 229.0 (M+H).

The following intermediate was prepared in accordance with the proceduredescribed in the above Scheme 9.

6-Bromo-8-fluoroimidazo[1,2-a]pyridine (LVI): Beige solid (909.0 mg,4.228 mmol, 80.7% yield). ¹ESIMS found for C₇H₄BrFN₂ m/z 214.9 (M+H).

Preparation of intermediate1-(6-bromoimidazo[1,2-a]pyridin-3-yl)-N,N-dimethylmethanamine (LX) isdepicted below in Scheme 10.

Step 1

To a solution of NaBH₄ (680 mg, 18.47 mmol) in MeOH (0.67 mL) was added6-bromoimidazo[1,2-a]pyridine-3-carbaldehyde (LVII) (2.05 g, 9.11 mmol).The reaction mixture was stirred overnight at room temperature. Thereaction mixture was concentrated, and the resulting residue wasadsorbed on silica gel, purified by column chromatography (0→10%MeOH/CHCl₃). Pure fractions were collected and concentrated, resultingsolids were triturated with DCM/hexane, filtered and dried under highvacuum to obtain (6-bromoimidazo[1,2-a]pyridin-3-yl)methanol (LVIII)(1.541 g, 6.787 mmol, 74.5% yield) as a beige solid. ESIMS found forC₈H₇BrN₂O m/z 226.9 (M+H).

Step 2

A mixture of SOCl₂ (1.5 mL, 20.68 mmol),(6-bromoimidazo[1,2-a]pyridin-3-yl)methanol (LVIII) (1.54 g, 6.78 mmol)in DCM (10 mL) was stirred for 12 h at 60° C. The reaction mixture wasconcentrated and dried under high vacuum to obtain6-bromo-3-(chloromethyl)imidazo[1,2-a]pyridine (LIX) (1.7 g, 6.92 mmol,102.1% yield) as a brown solid used without further for next step. ESIMSfound for C₈H₆BrClN₂ m/z 244.9 (M+H).

Step 3

A mixture of 6-bromo-3-(chloromethyl)imidazo[1,2-a]pyridine (LIX) (600mg, 2.44 mmol), K₂CO₃ (680 mg, 4.92 mmol) and N-methylmethanamine (0.33mL, 4.98 mmol) in MeCN (10 mL) was stirred for 12 h at 110° C. Thereaction mixture was concentrated resulting residue was adsorbed onsilica gel, purified by column chromatography (0→10% MeOH/CHCl₃). Purefractions were collected and concentrated, and dried under high vacuumto obtain 1-(6-bromoimidazo[1,2-a]pyridin-3-yl)-N,N-dimethylmethanamine(LX) (250 mg, 0.984 mmol, 40.3% yield) as a beige solid. ESIMS found forC₁₀H₁₂BrN₃ m/z 253.95 (M+H).

Preparation of intermediate5-bromo-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (LXIV) isdepicted below in Scheme 11.

Step 1

To a solution of 5-bromopyrazolo[1,5-a]pyridine (LXI) (commerciallyavailable from Synthonix) (0.36 g, 1.83 mmol) in MeOH (10 mL) was added1-iodopyrrolidine-2,5-dione (0.41 g, 1.83 mmol) slowly at 0° C. Themixture was stirred at 0° C. for 30 min, then warmed to room temperatureand stirred for 16 h. The mixture was concentrated in vacuo and theresidue was dissolved in DCM. The organics were washed with an aqueoussolution of saturated Na₂S₂O₃. The organics were then concentrated invacuo to afford 5-bromo-3-iodopyrazolo[1,5-a]pyridine (LXII) (526.0 mg,1.629 mmol, 89.1% yield) as a white solid. ESIMS found for C₇H₄BrIN₂ m/z322.8 (⁷⁹BrM+H).

Step 2

A mixture of1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(LXIII) (230 mg, 1.11 mmol), Pd(dppf)Cl₂ (80 mg, 0.090 mmol) and5-bromo-3-iodopyrazolo[1,5-a]pyridine (LXII) (300 mg, 0.930 mmol) wastaken in 1,4-dioxane (4 mL) and 2 M aqueous solution of K₃PO₄ (1.4 mL,2.8 mmol) was added. N₂ gas was purged for 5 min. The reaction mixturewas heated to 16 h at 80° C. The reaction was then cooled andconcentration under vacuum. The residue was purified via columnchromatography (0→8% MeOH/CHCl₃) (12 g of silica gel) to produce5-bromo-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (LXIV) (68mg, 0.245 mmol, 26.4% yield) as a yellow solid. ESIMS found forC₁₁H₉BrN₄ m/z 276.95 (⁷⁹BrM+H).

The following intermediate was prepared in accordance with the proceduredescribed in the above Scheme 11.

5-Bromo-3-(pyridin-3-yl)pyrazolo[1,5-a]pyridine (LXV): Beige solid (150mg, 0.547 mmol, 35.3% yield). ESIMS found for C₁₂H₈BrN₃ m/z 273.9 (M+H).

Preparation of intermediate(5-bromopyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone(LXVIII) is depicted below in Scheme 12.

Step 1

A mixture of 5-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid (LXVI)(Commercially available from Advanced ChemBlocks Inc.) (300 mg, 1.24mmol), DIPEA (0.44 mL, 2.53 mmol), and HATU (0.47 g, 1.24 mmol) in DMF(4 mL) was stirred at room temperature for 5 min. Then,1-methylpiperazine (LXVII) (0.28 mL, 2.52 mmol) was added and thereaction mixture was continued at room temperature for 5 h. The solventswere concentrated in vacuo, the residue taken into EtOAc, washed withwater, saturated aqueous NaHCO₃, water, and brine. The organic layerswere dried over anhydrous Na₂SO₄, then concentrated and under high vacuoto obtain crude(5-bromopyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone(LXVIII) (335 mg, 1.037 mmol, 83.3% yield) as a brown gummy solid, whichwas used in the next step without purification. ESIMS found forC₁₃Hl₅BrN₄O m/z 323.0 (⁷⁹BrM+H).

The following intermediates were prepared in accordance with theprocedure described in the above Scheme 12.

(5-Bromopyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone (LXIX):Off-white solid (123.0 mg, 0.397 mmol, 95.6% yield). ESIMS found forC₁₂H₁₂BrN₃O₂ m/z 310.95 (M+H).

(5-Bromopyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone (LXX):Light brown solid (121.0 mg, 0.393 mmol, 94.6% yield). ESIMS found forC₁₃H₁₄BrN₃O m/z 308.0 (M+H).

(5-Bromopyrazolo[1,5-a]pyridin-3-yl)(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)methanone(LXXI): Beige solid (36 mg, 0.103 mmol, 24.8% yield). ESIMS found forC₁₅H₁₇BrN₄O m/z 349.0 (M+H).

(5-Bromopyrazolo[1,5-a]pyridin-3-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone(LXXII): Beige solid (155 mg, 0.444 mmol, 107.0% yield). ESIMS found forC₁₅H₁₇BrN₄O m/z 349.0 (M+H).

tert-Butyl7-(5-bromopyrazolo[1,5-a]pyridine-3-carbonyl)-4,7-diazaspiro[2.5]octane-4-carboxylate(LXXIII): White foam (320 mg, 0.735 mmol, 88.6% yield). ESIMS found forC₁₉H₂₃BrN₄O₃ m/z 435.0 (M+H).

(5-Bromopyrazolo[1,5-a]pyridin-3-yl)(4-cyclopropylpiperazin-1-yl)methanone(LXXIV): White solid (145 mg, 0.415 mmol, 100.1% yield). ESIMS found forC₁₅H₁₇BrN₄O m/z 349.1 (M+H).

(5-Bromopyrazolo[1,5-a]pyridin-3-yl)(4-(4-methylpiperazin-1-yl)piperidin-1-yl)methanone(LXXV): White solid (112 mg, 0.276 mmol, 66.4% yield). ESIMS found forC₁₈H₂₄BrN₅O m/z 406.1 (M+H).

(5-Bromopyrazolo[1,5-a]pyridin-3-yl)(4-morpholinopiperidin-1-yl)methanone(LXXVI): White solid (162 mg, 0.412 mmol, 99.2% yield). ESIMS found forC₁₇H₂₁BrN₄O₂ m/z 393.1 (M+H).

tert-Butyl6-(5-bromopyrazolo[1,5-a]pyridine-3-carbonyl)-2,6-diazaspiro[3.3]heptane-2-carboxylate(LXXVII): White solid (323 mg, 0.767 mmol, 92.4% yield). ESIMS found forC₁₈H₂₁BrN₄O₃ m/z 421.1 (M+H).

tert-Butyl5-(5-bromopyrazolo[1,5-a]pyridine-3-carbonyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate(LXVIII): Clear viscous solid (152 mg, 0.349 mmol, 84.2% yield). ESIMSfound for C₁₉H₂₃BrN₄O₃ m/z 379.0 (M+H-^(t)Bu).

5-Bromo-N-(2,2-difluoroethyl)pyrazolo[1,5-a]pyridine-3-carboxamide(LXXIX): White sold (506 mg, 1.66 mmol, 87.2% yield). ESIMS found forC₁₀H₈BrF₂N₃O m/z 304.0 (M+H).

(R)-5-Bromo-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide(LXXX): White sold (280 mg, 0.833 mmol, 100.4% yield). ESIMS found forC₁₁H₉BrF₃N₃O m/z 336.0 (M+H).

tert-Butyl3-((5-bromopyrazolo[1,5-a]pyridine-3-carboxamido)methyl)-3-fluoroazetidine-1-carboxylate(LXXXI): White sold (244 mg, 0.572 mmol, 69.0% yield). ESIMS found forC₁₇H₂₀BrFN₄O₃ m/z 385.0 (M+H-^(t)Bu+Me).

tert-Butyl(3R,4R)-4-(5-bromopyrazolo[1,5-a]pyridine-3-carboxamido)-3-fluoropiperidine-1-carboxylate(LXXXII): Clear viscous sold (370 mg, 0.839 mmol, 101.1% yield). ESIMSfound for C₁₈H₂₂BrFN₄O₃ m/z 385.0 (M+H-^(t)Bu).

5-Bromo-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide(LXXXIII): White sold (157.0 mg, 0.466 mmol, 112.2% yield). ESIMS foundfor C₁₄H₁₇BrN₄O m/z 337.0 (M+H).

5-Bromo-N-methyl-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide(LXXXIX): Clear viscous sold (150 mg, 0.427 mmol, 102.9% yield). ESIMSfound for C₁₅H₁₉BrN₄O m/z 351.1 (M+H).

5-Bromo-N-(1-cyclopropylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide(XC): Beige sold (95 mg, 0.262 mmol, 63.0% yield). ESIMS found forC₁₆H₁₉BrN₄O m/z 363.0 (M+H).

5-Bromo-N-(1-(cyclopropylmethyl)piperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide(XCI): White sold (157 mg, 0.416 mmol, 100.3% yield). ESIMS found forC₁₇H₂₁BrN₄O m/z 377.1 (M+H).

5-Bromo-N-(1-(2,2-difluoropropyl)piperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide(XCII): Orange viscous sold (170 mg, 0.424 mmol, 102.1% yield). ESIMSfound for C₁₆H₁₉BrF₂N₄O m/z 401.1 (M+H).

5-Bromo-N-(1-(2-methoxyethyl)piperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide(XCIII): White sold (240 mg, 0.630 mmol, 75.9% yield). ESIMS found forC₁₆H₂₁BrN₄O₂ m/z 381.1 (M+H).

5-Bromo-N-(1-(pyridin-2-ylmethyl)piperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide(XCIV): White sold (218 mg, 0.526 mmol, 84.6% yield). ¹ESIMS found forC₁₉H₂₀BrN₅O m/z 414.1 (M+H).

5-Bromo-N-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide(XCV): White solid (85 mg, 0.262 mmol, 63.2% yield). ESIMS found forC₁₃H₁₄BrN₃O₂ m/z 324.0 (M+H).

5-Bromo-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide (XCVI):Light brown solid (86.0 mg, 0.271 mmol, 65.4% yield). ESIMS found forC₁₃H₉BrN₄O m/z 316.9 (M+H).

6-Bromo-N-(1-methylpiperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide(XCVII): Beige solid (349 g, 0.035 mmol, 99.8% yield). ESIMS found forC₁₄H₁₇BrN₄O m/z 337.0 (M+H).

6-Bromo-N-(2,2-difluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide(XCVIII): Light yellow solid (240 mg, 0.789 mmol, 95.1% yield). ESIMSfound for C₁₀H₈BrF₂N₃O m/z 304.0 (M+H).

(6-Bromoimidazo[1,2-a]pyrimidin-3-yl)(4-methylpiperazin-1-yl)methanone(XCIX): Gummy white solid (159 mg, 0.491 mmol, 59.4% yield). ESIMS foundfor C₁₂H₁₄BrN₅O m/z 324.0 (M+H).

Preparation of intermediate imidazo[1,2-a]pyrimidin-6-ylboronic acid(CII) is depicted below in Scheme 13.

Step 1

A mixture of5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (C) (1g, 4.52 mmol) and chloroacetaldehyde (CI) (0.92 mL, 5.39 mmol) wasdissolved in 1,4-dioxane (20 mL) and heated to 110° C. over the weekend.The reaction mixture was cooled, and the solids were collected byfiltration and dried under high vacuo to obtainimidazo[1,2-a]pyrimidin-6-ylboronic acid (CII) (650 mg, 3.989 mmol,88.2% yield) as a brown solid which was used for next step withoutpurification. ESIMS found for C₆H₆BN₃O₂ m/z 164.1 (M+H).

Preparation of intermediate6-bromo-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine (CVII) isdepicted below in Scheme 14.

Step 1

A mixture of 2-aminopropane (CIV) (0.86 mL, 9.96 mmol),5-bromo-3-fluoro-2-nitropyridine (CIII) (2 g, 9.05 mmol) and K₂CO₃ (2.5g, 18.1 mmol) in MeCN (40 mL) was stirred at room temperature for 16 h.The reaction mixture was added to water (200 mL), stirred for 1 h andthe resulting solids were collected by filtration and dried under highvacuo to obtain 5-bromo-N-isopropyl-2-nitropyridin-3-amine (CV) (2.36 g,9.074 mmol, 100.3% yield) as a yellow solid which was used for next stepwithout purification. ESIMS found for C₈H₁₀BrN₃O₂ m/z 260.0 (M+H).

Step 2

A mixture of 5-bromo-N-isopropyl-2-nitropyridin-3-amine (CV) (2.35 g,9.04 mmol) Fe (5.91 g, 90.35 mmol) and NH₄Cl (7.25 g, 135.53 mmol) wastaken in a mixture of EtOH (30 mL) and water (10 mL) and the mixture washeated to 70° C. for 2 h. The reaction mixture was cooled, filteredthrough Celite®, filtrates were taken into EtOAc, washed with water thenbrine, dried over anhydrous Na₂SO₄, filtered, and concentrated underreduced pressure to obtain 5-bromo-N³-isopropylpyridine-2,3-diamine(CVI) (2.2 g, 9.561 mmol, 105.8% yield) as a dark brown solid which wasused for next step without purification. ESIMS found for C₈H₁₂BrN₃ m/z230.05 (M+H).

Step 3

A solution of 5-bromo-N³-isopropylpyridine-2,3-diamine (CVI) (2.08 g,9.04 mmol) and Ac₂O (1.05 mL, 10.84 mmol) in HOAc (20 mL) was heated to120° C. for 16 h. The reaction mixture was concentrated, the residuepartitioned between EtOAc/1 N NaOH, organics separated, washed withwater and brine. The organics were dried over anhydrous Na₂SO₄, solventsconcentrated and dried under high vacuo to give6-bromo-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine (CVII) (1.57 g,6.178 mmol, 68.3% yield) as a dark brown solid which was used for nextstep without purification. ESIMS found for C₁₀H₁₂BrN₃ m/z 254.0 (M+H).

Preparation of intermediate6-bromo-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole(CXIII) is depicted below in Scheme 15.

Step 1

A mixture of tert-butyl 4-aminopiperidine-1-carboxylate (CIX)(commercially available from Combi-Blocks Inc.) (1.68 g, 8.4 mmol),5-bromo-1,3-difluoro-2-nitrobenzene (CVIII) (commercially available fromCombi-Blocks Inc.) (2 g, 8.4 mmol) and K₂CO₃ (2.32 g, 16.81 mmol) inMeCN (40 mL) was stirred at room temperature over the weekend. Thesolvents were concentrated, and the residue partitioned betweenEtOAc/water. The organics were separated and washed with water and brinesolution. The organics were dried over anhydrous Na₂SO₄, solventsremoved in vacuo and the crude was purified by ISCO (0→30%EtOAc/hexanes) to obtain tert-butyl4-((5-bromo-3-fluoro-2-nitrophenyl)amino) piperidine-1-carboxylate (CX)(2.564 g, 6.130 mmol, 72.9% yield) as a yellow solid. ESIMS found forC₁₆H₂₁BrFN₃O₄ m/z 362.05 (M+H-tBu).

Step 2

To a solution of tert-butyl 4-((5-bromo-3-fluoro-2-nitrophenyl)amino)piperidine-1-carboxylate (CX) (2.6 g, 6.22 mmol) and NH₄Cl (4.99 g,93.24 mmol) in a mixture of acetone (75 mL)and water (15 mL) was addedzinc powder (4.06 g, 62.16 mmol) (three equal portions over 5 minutes)at 0° C. The mixture was stirred until reaction had warmed to 23° C. Themixture was filtered through Celite® and the solvents were concentratedunder high vacuum. The mixture was re-dissolved in EtOAc and filtered asecond time through Celite® and the filtrates were washed with water andbrine, dried over anhydrous Na₂SO₄, filtered, and concentrated underreduced pressure to obtain tert-butyl4-((2-amino-5-bromo-3-fluorophenyl)amino)piperidine-1-carboxylate (CXI)(2.41 g, 6.207 mmol, 99.8% yield) as a light brown solid. The resultantresidue was used in the next reaction without further purification.ESIMS found for C₁₆H₂₃BrFN₃O₂ m/z 332.0 (M+H-tBu).

Step 3

A solution of tert-butyl 4-((2-amino-5-bromo-3-fluorophenyl)amino)piperidine-1-carboxylate (CXI) (900 mg, 2.32 mmol) in HOAc (12 mL) washeated to 120° C. for 16 h. The reaction mixture was concentrated, theresidue treated with 7 N NH₃/MeOH, absorbed on silica and was purifiedby ISCO (0→8% 7 N NH₃ in MeOH/CHCl₃) to obtain6-bromo-4-fluoro-2-methyl-1-(piperidin-4-yl)-1H-benzo[d]imidazole (CXII)(510 mg, 1.634 mmol, 70.5% yield) as a brown solid. ESIMS found forC₁₃H₁₅BrFN₃ m/z 312.1 (M+H).

Step 4

To a stirred solution of6-bromo-4-fluoro-2-methyl-1-(piperidin-4-yl)-1H-benzo[d]imidazole (CXII)(510 mg, 1.63 mmol) in MeOH (8 mL) was added formaldehyde (0.41 mL, 2.04mmol). After 15 min, NaBH(OAc)₃ (520 mg, 2.45 mmol) was added, and themixture was stirred at room temperature for 2 h. LC-MS of the mixtureshowed completion of the reaction. The solvents were concentrated, theresidue taken up in chloroform, washed with 1 N NaOH, water and brinesolution. The organics were dried over anhydrous Na₂SO₄, solventsremoved and dried under high vacuo to obtain crude6-bromo-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole(CXIII) (440 mg, 1.349 mmol, 82.5% yield) as a light brown solid whichwas used in the next step without purification. ESIMS found forC₁₄H₁₇BrFN₃ m/z 326. (M+H).

Preparation of intermediate6′-bromospiro[cyclohexane-1,1′-isoindolin]-3′-one (CXIX) is depictedbelow in Scheme 16.

Step 1

A mixture of methyl 4-bromo-2-(bromomethyl)benzoate (CXIV) (5 g, 16.24mmol), 4-methoxybenzylamine (CXV) (4.25 mL, 32.75 mmol) and K₂CO₃ (9.02g, 65.26 mmol) in toluene (100 mL) was heated to 95° C. for 16 h. Thereaction mixture was cooled to room temperature, added to water (200mL), and extracted with EtOAc. The insoluble solids were collected byfiltration (product not soluble, 1.25 g), organic layer separated,washed with brine, dried over anhydrous Na₂SO₄, and the solvents wereconcentrated in vacuo. The residue was suspended in EtOAc (50 mL),sonicated, the solids collected by filtration, washed with diethylether, and dried under high vacuo to obtain5-bromo-2-[(4-methoxyphenyl)methyl]-3H-isoindol-1-one (CXVI) (3.86 g,11.62 mmol, 71.6% yield) as a white solid. ESIMS found for C₁₆H₁₄BrNO₂m/z 332.0 (M+H).

Step 2

To a stirred suspension of5-bromo-2-[(4-methoxyphenyl)methyl]-3H-isoindol-1-one (CXVI) (1.0 g,3.01 mmol) in DMF (15 mL) was added NaH (301 mg, 7.53 mmol) and themixture was stirred for 20 min. 1,5-Diiodopentane (CXVII) (0.58 mL, 3.9mmol) was then added, and the mixture was stirred at room temperaturefor 16 h. The reaction mixture was added to water (150 mL), extractedwith EtOAc, washed with brine, dried over anhydrous Na₂SO₄, solventsconcentrated, and the crude was purified by ISCO (0→60% EtOAc/hexanes)to obtain5′-bromo-2′-[(4-methoxyphenyl)methyl]spiro[cyclohexane-1,3′-isoindole]-1′-one(CXVIII) (0.37 g, 0.92 mmol, 30.7% yield) as a colorless thick syrup.ESIMS found for C₂₁H₂₂BrNO₂ m/z 400.1 (M+H).

Step 3

A solution of5′-bromo-2′-[(4-methoxyphenyl)methyl]spiro[cyclohexane-1,3′-isoindole]-1′-one(CXVIII) (0.37 g, 0.92 mmol) in TFA (4 mL) was heated to 90° C. for 16 hThe solvents were concentrated, treated with 7 N NH₃/MeOH and theresidue was purified by ISCO (20→100% 10% 7 N NH₃ MeOH in CHCl₃/CHCl₃)to obtain 6′-bromospiro[cyclohexane-1,1′-isoindolin]-3′-one (CXIX) (135mg, 0.482 mmol, 52.1% yield) as a beige solid. ESIMS found forC₁₃H₁₄BrNO m/z 280.0 (M+H).

Preparation of intermediate 8-bromo-4-methyl-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (CXXIII) is depicted below in Scheme 17.

Step 1

Oxalyl chloride (348 mg, 2.74 mmol) was added to the cold solution of4-bromo-2-fluorobenzoic acid (CXX) (500 mg, 2.28 mmol) in DCM (6 mL).Two drops of DMF was then added and allowed to stir for about 30 min.Solvents were removed and kept under vacuum for about 30 min.Redissolved in DCM (6 mL) and added 2-(methylamino)ethanol (CXXI) (39mg, 5.25 mmol). The reaction was stirred at room temperature for 3 h.The reaction was concentrated and purified on column (20→100%EtOAc/hexanes), pure fractions were combined and concentrated to yield4-bromo-2-fluoro-N-(2-hydroxyethyl)-N-methylbenzamide (CXXII) (525 mg,1.902 mmol, 83.3% yield) as a white solid. ESIMS found for C₁₀H₁₁BrFNO₂m/z 276.0 (M+H).

Step 2

To a solution of 4-bromo-2-fluoro-N-(2-hydroxyethyl)-N-methylbenzamide(CXXII) (525 mg, 1.9 mmol) dissolved in DMF (8 mL) was added Cs₂CO₃(1.239 g, 3.8 mmol). The reaction was stirred at 100° C. overnight.LC/MS suggest almost 80% conversion. Water was added, filtered, and thesolid purified on column (0→70% EtOAc/hexanes) to give8-bromo-4-methyl-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (CXXIII)(254 mg, 0.992 mmol, 52.2% yield) as a white solid. ESIMS found forC₁₀H₁₀BrNO₂ m/z 256.0 (M+H).

Preparation of intermediate6-bromo-4-(4-methylpiperazin-1-yl)quinazoline (CXXV) is depicted belowin Scheme 18.

Step 1

To a stirred suspension of 6-bromo-4-chloroquinazoline (CXXIV)(commercially available from Enamine Ltd) (0.5 g, 2.05 mmol) in IPA (5mL) was added DIPEA (0.72 mL, 4.13 mmol) and 1-methylpiperazine (LXVII)(632.1 mg, 6.310 mmol). The mixture becomes clear solution in fewminutes and was heated to 75° C. for 1.5 h. The solvents wereconcentrated, the residue partitioned between EtOAc/water, organicsseparated, washed with brine, dried over anhydrous Na₂SO₄, solventsconcentrated and dried under high vacuo to obtain crude6-bromo-4-(4-methylpiperazin-1-yl)quinazoline (CXXV) (645.0 mg, 2.100mmol, 102.3% yield) as a thick brown gum which was used for next thestep without purification. ESIMS found for C₁₃H₁₅BrN₄ m/z 307.0 (M+H).

Preparation of intermediate7-bromo-2-((1-methylpiperidin-4-yl)oxy)quinoxaline (CXXVIII) is depictedbelow in Scheme 19.

Scheme 19 Step 1

A mixture of 1-methyl-4-piperidinol (CXXVII) (0.36 g, 3.13 mmol), Cs₂CO₃(1.34 g, 4.11 mmol) and 7-bromo-2-chloro-quinoxaline (CXXVI)(commercially available from Enamine Ltd) (0.5 g, 2.05 mmol) in DMF (6mL) was heated to 90° C. overnight. The solvents were concentrated, andthe residue partitioned between EtOAc/water. The organic layer wasseparated, washed with brine, dried over anhydrous Na₂SO₄, concentrated.The residue was purified by ISCO (0→50% 10% 7 N NH₃ in MeOH inCHCl₃/CHCl₃). The pure fractions were concentrated, dried under highvacuo to obtain 7-bromo-2-(1-methylpiperidin-4-yl)oxyquinoxaline(CXXVIII) (293.0 mg, 0.909 mmol, 44.3% yield) as a beige solid. ESIMSfound for C₁₄H₁₆BrN₃O m/z 322.0 (M+H).

The following intermediate was prepared in accordance with the proceduredescribed in the above Scheme 19.

6-Bromo-4-((1-methylpiperidin-4-yl)oxy)quinazoline (CXXIX): Off-whitesolid (293 mg, 0.909 mmol, 44.3% yield). ESIMS found for C₁₄H₁₆BrN₃O m/z322.0 (M+H).

Preparation of intermediate7-bromo-N-(1-methylpiperidin-4-yl)quinoxalin-2-amine (CXXXI) is depictedbelow in Scheme 20.

Step 1

To a microwave vial was added 7-bromo-2-chloro-quinoxaline (CXXX)(commercially available from Combi-Blocks Inc.) (100 mg, 0.41 mmol),4-amino-1-methylpiperidine (LI) (94 mg, 0.82 mmol), K₂CO₃ (170 mg, 1.23mmol) and MeCN (2 mL). The reaction mixture was irradiated at 90° C. for16 h. The reaction was cooled, filtered, and concentrated under vacuum.The crude product was dissolved in DCM, washed with water, brine, driedover anhydrous MgSO₄, and filtered to produce7-bromo-N-(1-methylpiperidin-4-yl)quinoxalin-2-amine (CXXXI) (95 mg,0.296 mmol, 72.0% yield) as a beige solid. Carried onto the next stepwithout further purification. ESIMS found for C₁₄H₁₇BrN₄ m/z 321.0(M+H).

The following intermediates were prepared in accordance with theprocedure described in the above Scheme 20.

6-Bromo-N-(1-methylpiperidin-4-yl)quinazolin-4-amine (CXXXII): Tan solid(105 mg, 0.327 mmol, 79.6% yield). ESIMS found for C₁₄H₁₇BrN₄ m/z 321.0(M+H).

6-Bromo-N-(6-methoxypyridin-3-yl)quinazolin-4-amine (CXXXIII): Yellowsolid (109 mg, 0.329 mmol, 80.1% yield). ESIMS found for C₁₄H₁₁BrN₄O m/z330.9 (M+H).

6-Bromo-N-(6-((1-methylpiperidin-4-yl)oxy)pyridin-3-yl)quinazolin-4-amine(CXXXIV): Light brown solid (308 mg, 0.743 mmol, 90.5% yield). ESIMSfound for C₁₉H₂₀BrN₅O m/z 414.0 (M+H).

6-Bromo-N-(pyridin-3-ylmethyl)quinazolin-4-amine (CXXXV): Yellow solid(587 mg, 1.863 mmol, 90.7% yield). ESIMS found for C₁₄H₁₁BrN₄ m/z 314.95(M+H).

6-Bromo-N-((6-(4-methylpiperazin-1-yl)pyridin-3-yl)methyl)quinazolin-4-amine(CXXXVI): White solid (270 mg, 0.653 mmol, 79.5% yield). ESIMS found forC₁₉H₂₁BrN₆ m/z 413.0 (M+H).

6-Bromo-N-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)methyl)quinazolin-4-amine(CXXXVII): White solid (455 mg, 1.101 mmol, 89.4% yield). ESIMS foundfor C₁₉H₂₁BrN₆ m/z 413.0 (M+H).

tert-Butyl7-(6-bromoquinazolin-4-yl)-4,7-diazaspiro[2.5]octane-4-carboxylate(CXXXVIII): Yellow solid (800 mg, 1.908 mmol, 92.9% yield). ESIMS foundfor C₁₉H₂₃BrN₄O₂ m/z 419.0 (M+H).

tert-Butyl8-(6-bromoquinazolin-4-yl)-5,8-diazaspiro[3.5]nonane-5-carboxylate(CXXXIX): Beige solid (500 mg, 1.353 mmol, 54.9% yield). ESIMS found forC₂₀H₂₅BrN₄O₂ m/z 333.0 (M+H-Boc).

tert-Butyl9-(6-bromoquinazolin-4-yl)-6,9-diazaspiro[4.5]decane-6-carboxylate(CXL): Beige solid (750 mg, 2.160 mmol, 105.2% yield). ESIMS found forC₂₁H₂₇BrN₄O₂ m/z 347.0 (M+H-Boc).

Preparation of intermediate tert-butyl7-(6-bromoquinoline-4-carbonyl)-4,7-diazaspiro[2.5]octane-4-carboxylate(CXLIII) is depicted below in Scheme 21.

Step 1

To a suspension of tert-butyl 4,7-diazaspiro[2.5]octane-4-carboxylate(CXLII) (commercially available from Combi-Blocks Inc.) (620 mg, 2.92mmol), 6-bromoquinoline-4-carboxylic acid (CXLI) (commercially availablefrom Combi-Blocks Inc.) (0.7 g, 2.78 mmol), DMAP (150 mg, 1.23 mmol) andHATU (1.2 g, 3.16 mmol) in DMF (7 mL) was added DIPEA (1 mL, 5.74 mmol).The resulting mixture was stirred at 80° C. for 3 h. The mixture wascooled to room temperature and added into the water. The resulting solidwas filtered and dried under high vacuo to afford tert-butyl7-(6-bromoquinoline-4-carbonyl)-4,7-diazaspiro[2.5]octane-4-carboxylate(CXLIII) (1.1 g, 2.465 mmol, 88.7% yield) as a brown solid. ESIMS foundfor C₂₁H₂₄BrN₃O₃ m/z 446.0 (M+H).

The following intermediates were prepared in accordance with theprocedure described in the above Scheme 21.

6-Bromo-N-(1-methylpiperidin-4-yl)quinoline-4-carboxamide (CXLIV): Whitesolid (210 mg, 0.603 mmol, 50.7% yield). ESIMS found for C₁₆H₁₈BrN₃O m/z348.0 (M+H).

6-Bromo-N-(1-methylpiperidin-4-yl)quinazoline-4-carboxamide (CXLV):Brown solid (300 mg, 0.859 mmol, 72.5% yield). ESIMS found forC₁₅H₁₇BrN₄O m/z 349.0 (M+H).

tert-Butyl7-(6-bromoquinazoline-4-carbonyl)-4,7-diazaspiro[2.5]octane-4-carboxylate(CXLVI): Brown solid (279 mg, 0.604 mmol, 76.4% yield). ESIMS found forC₂₀H₂₃BrN₄O₃ m/z 447.0 (M+H).

Example 1

Preparation of2-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine (7) isdepicted below in Scheme 22.

Step 1

A mixture of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (CXLVII)(commercially available from Combi-Blocks Inc.) (100 mg, 0.68 mmol),sulfur (44 mg, 1.37 mmol) and 3,4-diaminopyridine (CXLVIII) (75 mg, 0.69mmol) in DMA (2 mL) was heated to 120° C. for 3 h. The solvent wasevaporated the crude residue was absorbed on silica gel and purified bycolumn chromatography (10% 7 N NH₃ MeOH/CHCl₃) to obtain2-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine (7) (20 mg,0.085 mmol, 12.4% yield) as a beige solid. ¹H NMR (499 MHz, DMSO-d₆) δppm 7.29 (1H, dd, J=7.82, 4.53 Hz), 7.55 (1H, br s), 8.28 (1H, d, J=5.49Hz), 8.33 (1H, br s), 8.36 (1H, dd, J=4.53, 1.51 Hz), 8.79 (1H, dd,J=7.96, 1.37 Hz), 8.89 (1H, br s), 12.30 (1H, br s), 12.99 (1H, br s);ESIMS found for C₁₃H₉N₅ m/z 236.1 (M+1).

Example 2

Preparation of6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl) quinoline(186) is depicted below in Scheme 23.

Step 1

A mixture of N-tosyl-4-chloro-3-iodo-7-azaindole (CXLIX) (commerciallyavailable from Combi-Blocks Inc.) (500 mg, 1.16 mmol),quinoline-6-boronic acid (CL) (commercially available from Combi-BlocksInc.) (220 mg, 1.27 mmol), a 2 M aqueous solution of K₃PO₄ (1.7mL, 3.4mmol) and Pd(dppf)Cl₂ (50 mg, 0.06 mmol) in 1,4-dioxane (10 mL) waspurged with N₂ gas for 5 min. The mixture was stirred and irradiatedwith microwave at 80° C. for 30 min. The reaction mixture was cooled,and organic layer was separated, concentrated. The crude product waspurified by silica gel chromatography (0→10% MeOH/CHCl₃) to afford6-[4-chloro-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-3-yl]quinoline(CLI) (400 mg, 0.922 mmol, 79.8% yield) as a beige solid. ESIMS foundfor C₂₃H₁₆ClN₃O₂S m/z 434.0 (M+H).

Step 2

A mixture of6-[4-chloro-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-3-yl]quinoline(CLI) (50 mg, 0.12 mmol),1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (XLIII)(25 mg, 0.12 mmol), a 2 M aqueous solution of K₃PO₄ (0.17 mL, 0.34 mmol)and Pd(dppf)Cl₂ (5 mg, 0.01 mmol) in 1,4-dioxane (2 mL) was purged withN₂ gas for 5 min. The mixture was stirred and irradiated with microwaveat 110° C. for 30 min. The reaction mixture was cooled, and organiclayer was separated, concentrated to afford crude6-[1-(4-methylphenyl)sulfonyl-4-(1-methylpyrazol-4-yl)pyrrolo[2,3-b]pyridin-3-yl]quinoline(CLII) (60 mg, 0.1251 mmol, 108.6% yield) as a dark brown solid whichwas used in the next step without further purification. ESIMS found forC₂₇H₂₁N₅O₂S m/z 480.1 (M+H).

Step 3

A suspension of Cs₂CO₃ (205 mg, 0.63 mmol) and6-[1-(4-methylphenyl)sulfonyl-4-(1-methylpyrazol-4-yl)pyrrolo[2,3-b]pyridin-3-yl]quinoline(CLII) (60 mg, 0.13 mmol) in MeOH (0.94 mL) was heated at 75° C. for 2h. The reaction mixture was cooled and concentrated under vacuum. Thecrude was then purified by flash column chromatography (0→5%MeOH/CHCl₃). The desired fractions were concentrated to dryness in vacuoand the residue triturated in ether. The resulting solid was filteredand dried under high vacuo to afford6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl) quinoline(186) (20 mg, 0.062 mmol, 49.1% yield) as a beige solid. ¹H NMR (499MHz, DMSO-d₆) δ ppm 3.39 (3H, s), 7.10 (1H, d, J=4.94 Hz), 7.15 (1H, s),7.20 (1H, s), 7.45 (1H, dd, J=8.64, 2.06 Hz), 7.50 (1H, dd, J=8.23, 4.12Hz), 7.57 (1H, d, J=1.92 Hz), 7.76 (1H, d, J=2.47 Hz), 7.79 (1H, d,J=8.78 Hz), 8.08-8.16 (1H, m), 8.28 (1H, d, J=4.67 Hz), 8.85 (1H, dd,J=4.25, 1.78 Hz), 12.07 (1H, br s); ESIMS found for C₂₀H₁₅N₅ m/z 326.1(M+1).

Example 3

Preparation of6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine (280)is depicted below in Scheme 24.

Step 1

A mixture of 6-chloro-5-methyl-1H-pyrrolo[2,3-b]pyridine (CLIII)(commercially available from PharmaBlock (USA), Inc.) (1.05 g, 6.3mmol), and 1-iodopyrrolidine-2,5-dione (1.5 g, 6.67 mmol) in DMF (5 mL)was stirred at room temperature for 3 h. Reaction mixture wasconcentrated to remove most of the DMF and the residue was trituratedwith water, resulting solids were filtered, washed with MeOH, and driedto obtain 6-chloro-3-iodo-5-methyl-1H-pyrrolo[2,3-b]pyridine (CLIV)(1.57 g, 5.368 mmol, 85.2% yield) as a beige solid. ESIMS found forC₈H₆ClIN₂ m/z 292.9 (M+H).

Step 2

To a mixture of 6-chloro-3-iodo-5-methyl-1H-pyrrolo[2,3-b]pyridine(CLIV) (1.55 g, 5.3 mmol) in dry DMF (15 mL) was added NaH (500 mg, 12.5mmol) portionwise under N₂ at 0° C. The mixture was stirred at 0° C. for30 min. Tosyl chloride (CLV) (2.2 g, 11.54 mmol) was added portionwiseand stirring was continued at 0° C. for 1 h. Reaction mixture was slowlydiluted with water, precipitated solids were filtered, washed withaqueous saturated NaHC₃ and water. The collected solids were dried underhigh vacuum to obtain6-chloro-3-iodo-5-methyl-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine(CLVI) (2.1 g, 4.701 mmol, 88.7% yield) as a beige solid. ESIMS foundfor C₁₅H₁₂ClIN₂O₂S m/z 446.8 (M+H).

Step 3

A mixture of 6-chloro-3-iodo-5-methyl-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine (CLVI) (500 mg, 1.12 mmol),imidazo[1,2-a]pyridin-6-ylboronic acid, pinacol ester (CLVII)(commercially available from J&W Pharmlab) (300 mg, 1.23 mmol), a 2 Maqueous solution of K₃PO₄ (1.7 mL, 3.4 mmol) and Pd(dppf)Cl₂ (45 mg,0.06 mmol) in 1,4-dioxane (20 mL) was purged with N₂ gas for 5 min. Themixture was stirred and irradiated with microwave at 110° C. for 30 min.The reaction mixture was cooled, and organic layer was separated andconcentrated. The crude product was purified by silica gelchromatography (0→10% MeOH/CHCl₃) to afford6-chloro-3-imidazo[1,2-a]pyridin-6-yl-5-methyl-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine(CLVIII) (410 mg, 0.938 mmol, 83.8% yield) as a beige solid. ESIMS foundfor C₂₂H₁₇ClN₄O₂S m/z 437.0 (M+1).

Step 4

A solution of6-chloro-3-imidazo[1,2-a]pyridin-6-yl-5-methyl-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine(CLVIII) (100 mg, 0.23 mmol) in a solution of sodium ethoxide in EtOH (2mL, 5.1 mmol) was heated in a sealed tube at 100° C. for 12 h. Thereaction mixture was cooled to room temperature, carefully acidifiedwith 6 N HCl, extracted with EtOAc, washed with brine and concentrated.The residue was purified by ISCO (0→10% 7 N NH₃ in MeOH/CHCl₃). Purefractions were combined, concentrated, and the resulting solids wastriturated with DCM/hexanes, filtered and dried to produce6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine (280)(10 mg, 0.040 mmol, 17.6% yield) as a beige solid. ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.45 (3H, s), 7.56 (1H, d, J=1.09 Hz), 7.59-7.66 (2H, m),7.91 (1H, d, J=2.46 Hz), 8.00 (1H, s), 8.15 (1H, d, J=1.92 Hz), 8.21(1H, s), 8.90-8.96 (1H, m), 11.83 (1H, br s); ESIMS found for C₁₅H₁₂N₄m/z 249.05 (M+1).

Example 4

Preparation of4,4-dimethyl-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (435) is depicted belowin Scheme 25.

Step 1

To a stirred solution of 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde(CLIX) (commercially available from Combi-Blocks Inc.) (1 g, 3.68 mmol)in DMF (12 mL) was added sodium hydride (180 mg, 4.41 mmol) at 0° C. andthe mixture was stirred for 30 min. Then was added tosyl chloride (CLV)(770 mg, 4.05 mmol) in DMF (3 mL) and the mixture was stirred at roomtemperature for 3 h. The reaction mixture was added to water (100 mL)and stirred for 30 min. The resulting solids were collected byfiltration and dried under high vacuo to obtain3-iodo-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine-5-carbaldehyde(CLX) (1.93 g, 4.528 mmol, 123.2% yield) as an off-white solid. ESIMSfound for C₁₅H₁₁IN₂O₃S m/z 426.85 (M+H).

Step 2

A mixture of 1-methylpiperazine (LXVII) (0.26 mL, 2.34 mmol), HOAc (340mg, 5.63 mmol) and3-iodo-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine-5-carbaldehyde(CLX) (600 mg, 1.41 mmol) in a vial was stirred at room temperature for20 min. NaH(OAc)₃ (450 mg, 2.12 mmol) was then added and the mixture wasstirred at room temperature overnight. The reaction mixture wasconcentrated. EtOH (2 mL) and an additional 1-methylpiperazine (0.26 mL,2.34 mmol) and NaH(OAc)₃ (450 mg, 2.12 mmol) was added to a vial andheated at 50° C. overnight. The reaction was evaporated under vacuum andthe residue was absorbed on silica gel and was purified by ISCO (10→60%10% 7 N NH₃ MeOH/CHCl₃) to obtain3-iodo-1-(4-methylphenyl)sulfonyl-5-[(4-methylpiperazin-1-yl)methyl]pyrrolo[2,3-b]pyridine(CLXI) (250 mg, 0.490 mmol, 34.8% yield) as a light-yellow solid. ESIMSfound for C₂₀H₂₃IN₄O₂S m/z 510.95 (M+H).

Step 3

To a solution of bis(pinacolato)diboron (50 mg, 0.21 mmol) in1,4-dioxane (1 mL) was added6-bromo-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one (CLXII)(commercially available from Accela ChemBio Inc.) (50 mg, 0.19 mmol),KOAc (50 mg, 0.55 mmol) and SPhos Pd G4 (10 mg, 0.01 mmol). The mixturewas purged with N₂ for 1 min before heating at 90° C. under N₂ for 2 h.The reaction was cooled to room temperature and a 2 M aqueous solutionof K₃PO₄ (0.2 mL, 0.41 mmol),3-iodo-1-(4-methylphenyl)sulfonyl-5-[(4-methylpiperazin-1-yl)methyl]pyrrolo[2,3-b]pyridine(CLXI) (90 mg, 0.18 mmol), and SPhos Pd G4 (10 mg, 0.01 mmol) wereadded. The reaction was purged with N₂ and then heated at 100° C. underN₂ for 16 h. The reaction was concentrated under vacuum and the residuepurified via column chromatography (0→10% 7 N NH₃ in MeOH/CHCl₃) (4 g ofsilica gel) to yield4,4-dimethyl-6-[1-(4-methylphenyl)sulfonyl-5-[(4-methylpiperazin-1-yl)methyl]pyrrolo[2,3-b]pyridin-3-yl]-2,3-dihydroisoquinolin-1-one(CLXIII) (52 mg, 0.093 mmol, 52.9% yield) as an amber viscous solid.ESIMS found for C₃₁H₃₅N₅O₃S m/z 558.1 (M+1).

Step 4

A suspension of Cs₂CO₃ (150 mg, 0.45 mmol) and4,4-dimethyl-6-[1-(4-methylphenyl)sulfonyl-5-[(4-methylpiperazin-1-yl)methyl]pyrrolo[2,3-b]pyridin-3-yl]-2,3-dihydroisoquinolin-1-one(CLXIII) (50 mg, 0.09 mmol) in MeOH (1 mL) was heated at 75° C. for 2 h.The reaction mixture was cooled to room temperature and concentrated.The crude was then purified by flash column chromatography (0→10% 7 NNH₃ in MeOH/CHCl₃). The desired fractions were concentrated to drynessin vacuo and the residue triturated in ether. The resulting solid wasfiltered and dried under high vacuo to produce4,4-dimethyl-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one(435) (5 mg, 0.012 mmol, 13.8% yield) as a tan solid. ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.36 (6H, s), 2.13 (3H, d, J=1.92 Hz), 2.24-2.33 (4H, m),2.34-2.44 (4H, m), 3.21 (2H, d, J=2.74 Hz), 3.62 (2H, s), 6.40 (1H, dd,J=3.29, 1.92 Hz), 7.40-7.46 (1H, m), 7.66-7.70 (2H, m), 8.01 (1H, d,J=2.47 Hz), 8.18 (1H, s), 8.20 (1H, d, J=1.92 Hz), 12.00 (1H, br d,J=1.65 Hz); ESIMS found for C₂₄H₂₉N₅O m/z 404.1 (M+1).

Example 5

Preparation ofN-(5-fluoropyridin-3-yl)-3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide(764) is depicted below in Scheme 26.

Step 1

Starting with methyl 3-bromo-1H-pyrrolo[2,3-b]pyridine-5-carboxylate(XVI) (commercially available from PharmaBlock (USA), Inc.) protectionwas performed using procedure shown in Example 4, Scheme 25, Step 1 toyield methyl3-bromo-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine-5-carboxylate(XVII) (1.45 g, 3.543 mmol, 86.1% yield) as a beige solid. ESIMS foundfor C₁₅H₁₂F₃N₇ m/z 348.1 (M+1). ESIMS found for C₁₆H₁₃BrN₂O₄S m/z 409.0(M+H).

Step 2

Methyl3-bromo-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine-5-carboxylate(XVII) (290 mg, 0.71 mmol), tert-butyl3-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[2H-indene-1,4′-piperidine]-1′-carboxylate(CLXIV) (bromine analog is commercially available from 1 ClickChemistryInc.) (250 mg, 0.59 mmol), Pd(dppf)Cl₂ (25 mg, 0.03 mmol) and a 2 Maqueous solution of K₃PO₄ (0.6 mL, 1.2 mmol) in 1,4-dioxane (5 mL) waspurged with N₂ gas for 5 min. The mixture was stirred and irradiatedwith microwave at 110° C. for 30 min. The reaction mixture was cooleddown to room temperature, organic layer was separated and concentrated,and resulting residue was purified by column chromatography (0→5%MeOH/CHCl₃) to obtain tert-butyl6-[5-methoxycarbonyl-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-3-yl]-3-oxospiro[2H-indene-1,4′-piperidine]-1′-carboxylate(CLXV) (350 mg, 0.556 mmol, 95.0% yield) as a beige solid. ESIMS foundfor C₃₄H₃₅N₃O₇S m/z 630.3 (M+H).

Step 3

tert-Butyl6-[5-methoxycarbonyl-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-3-yl]-3-oxospiro[2H-indene-1,4′-piperidine]-1′-carboxylate(CLXV) (250 mg, 0.4 mmol) and a 2 M aqueous solution of NaOH (1 mL, 2.mmol) in MeOH (5 mL) was stirred at 50° C. for 12 h. Solvent wasevaporated, resulting residue was diluted with water, neutralized with 2N HCl, extracted with EtOAc, combined extracts were dried with anhydrousNa₂SO₄, and evaporated, to obtain3-[1′-[(2-methylpropan-2-yl)oxycarbonyl]-1-oxospiro[2H-indene-3,4′-piperidine]-5-yl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylicacid (CLXVI) (180 mg, 0.390 mmol, 98.2% yield) and as an off-whitesolids. ESIMS found for C₂₆H₂₇N₃O₅ m/z 462.2 (M+H).

Step 4

To a suspension of3-[1′-[(2-methylpropan-2-yl)oxycarbonyl]-1-oxospiro[2H-indene-3,4′-piperidine]-5-yl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylicacid (CLXVI) (180 mg, 0.39 mmol), 3-amino-5-fluoropyridine (CLXVII) (40mg, 0.39 mmol), HATU (220 mg, 0.58 mmol) and DMAP (0.g, 0.02 mmol) inDMF (1 mL) was added DIPEA (0.14 mL, 0.8 mmol). The resulting mixturewas stirred at 80° C. for 12 h. The reaction mixture was cooled anddiluted with water, precipitated solids were filtered and washed withwater. The collected solids was dried under high vacuum to affordtert-butyl6-[5-[(5-fluoropyridin-3-yl)carbamoyl]-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxospiro[2H-indene-1,4′-piperidine]-1′-carboxylate(CLXVIII) (75 mg, 0.135 mmol, 34.6% yield) as a brown solid. ESIMS foundfor C₃₁H₃₀FN₅O₄ m/z 556.25 (M+1).

Step 5

To a solution of TFA (0.5 mL, 6.49 mmol) in DCM (1 mL) was addedtert-butyl6-[5-[(5-fluoropyridin-3-yl)carbamoyl]-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxospiro[2H-indene-1,4′-piperidine]-1′-carboxylate(CLXVIII) (75 mg, 0.13 mmol). The mixture was stirred at roomtemperature overnight. The solvent was evaporated and resulting residuewas purified by column chromatography (0→10% 7 N NH₃ in MeOH/CHCl₃) toproduceN-(5-fluoropyridin-3-yl)-3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide(764) (20 mg, 0.044 mmol, 32.5% yield) as a beige solid. ¹H NMR (499MHz, DMSO-d₆) δ ppm 1.44 (2H, br d, J=12.62 Hz), 2.05 (2H, td, J=12.49,3.84 Hz), 2.62-2.71 (2H, m), 2.64 (2H, s), 2.98 (2H, br d, J=11.53 Hz),7.71 (1H, d, J=7.96 Hz), 7.89 (1H, dd, J=7.96, 1.37 Hz), 8.02 (1H, s),8.25 (1H, dt, J=11.39, 2.26 Hz), 8.29 (1H, s), 8.34 (1H, d, J=2.74 Hz),8.79-8.84 (1H, m), 8.88 (1H, d, J=1.92 Hz), 8.93 (1H, d, J=1.92 Hz),10.85 (1H, br s); ESIMS found for C₂₆H₂₂FN₅O₂ m/z 456.2 (M+1).

Example 6

Preparation of3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine(1384) is depicted below in Scheme 27.

Step 1

To a solution of5-bromo-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (LXIV) (70mg, 0.250 mmol) in 1,4-dioxane (1 mL) was added KOAc (80 mg, 0.770 mmol)and a 2 M aqueous solution of K₃PO₄ (0.3 mL, 0.600 mmol). The mixturewas bubbled with N₂ for 1 min before heating at 90° C. under N₂ for 2 h.The reaction was cooled to room temperature and5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (CLXIX)(commercially available from CombiBlocks) (0.12 g, 0.250 mmol),bis(pinacolato)diboron (80 mg, 0.300 mmol), and SPhos Pd G4 (10 mg,0.020 mmol) were added. The reaction was purged with N₂ and then heatedat 100° C. under N₂ for 16 h. The reaction was concentrated undervacuum. The residue was purified via column chromatography (0→8% 7 N NH₃in MeOH/CHCl₃) (12 g of silica gel) to yield5-bromo-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine(CLXX) (105 mg, 0.197 mmol, 79.3% yield) as an amber viscous solid.ESIMS found for C₂₄H₁₇BrN₆O₂S m/z 532.9 (⁷⁹BrM+H).

Step 2

To a stirred solution of5-bromo-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine(CLXX) (110 mg, 0.200 mmol) in 1,4-dioxane (3 mL) was added a 2 Maqueous solution of K₃PO₄ (0.25 mL, 0.500 mmol). Reaction mixture waspurged with argon before adding Pd(PPh₃)₄ (10 mg, 0.010 mmol) and1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine(CLXXI) (commercially available from CombiBlocks) (59.7 mg, 0.197 mmol).The reaction heated at 90° C. for 16 h under argon. The reaction wasconcentrated under vacuum and the residue purified via columnchromatography (0→8% 7 N NH₃ in MeOH/CHCl₃) (12 g of silica gel) toproduce3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine(CLXXII) (88 mg, 0.140 mmol, 71.0% yield) as a light orange solid. ESIMSfound for C₃₄H₃₁N₉O₂S m/z 630.1 (M+H).

Step 3

A suspension of Cs₂CO₃ (230 mg, 0.700 mmol) and3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine(CLXXII) (90 mg, 0.140 mmol) in MeOH (1 mL) was heated at 75° C. for 2h. The reaction mixture was cooled to room temperature and concentratedunder vacuum. The crude was then purified by flash column chromatography(0→10% 7 N NH₃ in MeOH/CHCl₃). The desired fractions were concentratedto dryness in vacuo and the residue triturated in ether. The resultingsolid was filtered and dried under high vacuo to afford3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine(1384) (5 mg, 0.010 mmol, 7.3% yield) as a light-yellow solid. ¹H NMR(499 MHz, DMSO-d₆) δ ppm 2.23 (3H, s), 2.42 (4H, t, J=4.94 Hz),3.56-3.62 (4H, m), 3.91 (3H, s), 7.08-7.14 (1H, m), 7.22 (1H, s), 7.39(1H, dd, J=7.27, 1.78 Hz), 7.94 (1H, s), 8.09 (1H, d, J=0.82 Hz), 8.20(1H, d, J=5.21 Hz), 8.20 (1H, s), 8.22 (1H, s), 8.26 (1H, s), 8.63 (1H,d, J=1.92 Hz), 8.66-8.71 (2H, m), 12.30 (1H, s); ESIMS found forC₂₈H₂₇N₉ m/z 490.1 (M+1).

Example 7

Preparation of6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole(1502) is depicted below in Scheme 28.

Step 1a-b

A mixture of6-bromo-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole(XXX) (150 mg, 0.460 mmol), bis(pinacolato)diboron (175 mg, 0.690 mmol),Pd(dppf)Cl₂ (37.6 mg, 0.050 mmol) and KOAc (135.4 mg, 1.38 mmol) wastaken in 1,4-dioxane (2 mL). N₂ gas was bubbled into the mixture for 3min and then was heated to 90° C. for 5 h. LC/MS of the mixture showedcompletion of the reaction. ESIMS found for C₂₀H₂₉BFN₃O₂ m/z 374.2(M+H).

To the reaction mixture was added3-bromo-6-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (CXIII)(commercially available from Advanced ChemBlocks Inc.) (171 mg, 0.460mmol), Pd(dppf)Cl₂ (37.6 mg, 0.050 mmol) and a 2 M aqueous solution ofK₃PO₄ (0.46 mL, 0.920 mmol). N₂ gas was bubbled for 5 min and then washeated to 90° C. for 16 h. The reaction mixture was added to a solutionof saturated aqueous NaHCO₃ (40 mL), extracted with EtOAc, organicsseparated, washed with water and brine. The organics were separated,dried over anhydrous Na₂SO₄, solvents concentrated, and the crude waspurified by ISCO (0→30% MeOH/CHCl₃) to obtain6-(6-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole(CLXXIII) (109 mg, 0.203 mmol, 44.1% yield) as a beige solid. ESIMSfound for C₂₇H₂₅ClFN₅O₂S m/z 538.2 (M+H).

Step 2

To a stirred solution of Pd(PPh₃)₄ (20 mg, 0.020 mmol) and6-(6-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole(CLXXIII) (110 mg, 0.200 mmol) in dry THF (0.5 mL) was added under N₂cyclopropylzinc(II) bromide (CLXXIV) (0.61 mL, 0.310 mmol) and themixture was heated to 70° C. for 16 h. LC/MS showed only 20% of theconversion. Additional equivalent of bromo(cyclopropyl)zinc (0.61 mL,0.310 mmol) was added and the mixture was heated to 70° C. for 24 h. Thereaction mixture was cooled, added to a solution of saturated aqueousNaHCO₃ and extracted with EtOAc. The organic layer was separated, washedwith water, brine and dried over anhydrous Na₂SO₄, solvents removed, andthe crude was purified by ISCO (0→30% MeOH/CHCl₃) followed by prep TLCto obtain6-(6-cyclopropyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole(CLXXV) (63 mg, 0.116 mmol, 57.2% yield) as a beige solid. ESIMS foundfor C₃₀H₃₀FN₅O₂S m/z 544. (M+H).

Step 3

A suspension of Cs₂CO₃ (189 mg, 0.580 mmol) and6-(6-cyclopropyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole(CLXXV) (63 mg, 0.120 mmol) in MeOH (1 mL) was heated at 75° C. for 5 h.The reaction mixture was cooled to room temperature and concentratedunder vacuum. The residue was dissolved in a mixture of CHCl₃/MeOH andthen purified by preparative TLC (6% 7 N NH₃ in MeOH/CHCl₃) to afford6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole(1502) (9 mg, 0.022 mmol, 19.2% yield) as a beige solid. ¹H NMR (499MHz, DMSO-d₆) δ ppm 0.94-0.99 (4H, m), 1.82-1.90 (2H, m), 2.10-2.20 (3H,m), 2.25 (3H, s), 2.42 (2H, qd, J=12.26, 3.57 Hz), 2.61 (3H, s), 2.94(2H, br d, J=11.25 Hz), 4.32 (1H, tt, J=12.35, 4.39 Hz), 7.12 (1H, d,J=8.23 Hz), 7.22-7.28 (1H, m), 7.58 (1H, d, J=1.10 Hz), 7.77 (1H, d,J=2.47 Hz), 8.07 (1H, d, J=7.96 Hz), 11.73 (1H, br s); ESIMS found forC₂₄H₂₆FN₅ m/z 404.2 (M+1).

Example 8

Preparation ofN-(3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide (1898) andN-(3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide(1899) are depicted below in Scheme 29.

Steps 1-2

A mixture of KOAc (240 mg, 2.45 mmol), tert-butyl6-bromo-3-oxo-2,3-dihydrospiro[indene-1,4-piperidine]-1-carboxylate(CLXXVI) (commercially available from 1 ClickChemistry Inc.) (300 mg,0.79 mmol), bis(pinacolato)diboron (240 mg, 0.95 mmol) and Pd(dppf)Cl₂(30 mg, 0.04 mmol) in 1,4-dioxane (10 mL) was bubbled with N₂ gas for 5min. The reaction was then heated to 90° C. for 5 h. Reaction mixturewas cooled before adding1-(benzenesulfonyl)-3-bromo-6-chloro-1H-pyrrolo[2,3-b]pyridine (XXX)(commercially available from Advanced ChemBlocks Inc.) (350 mg, 0.94mmol), a 2 M aqueous solution of K₂CO₃ (1.2 mL, 2.4 mmol), and anotherportion of Pd(dppf)Cl₂ (30 mg, 0.04 mmol). N₂ gas was bubbled into themixture for 5 min. and the mixture was stirred and irradiated withmicrowave at 110° C. for 30 min. The organic layer was separated andconcentrated, purified by ISCO (0-100% EtOAc/hexane) to obtaintert-butyl6-[1-(benzenesulfonyl)-6-chloropyrrolo[2,3-b]pyridin-3-yl]-3-oxospiro[2H-indene-1,4′-piperidine]-1′-carboxylate(CLXXVII) (317 mg, 0.535 mmol, 67.9% yield) as a beige solid. ESIMSfound for C₃₁H₃₀ClN₃O₅S m/z 592.05 (M+H).

Step 3

A mixture of tert-butyl6-[1-(benzenesulfonyl)-6-chloropyrrolo[2,3-b]pyridin-3-yl]-3-oxospiro[2H-indene-1,4′-piperidine]-1′-carboxylate(CLXXVII) (317 mg, 0.54 mmol), isonicotinamide (CLXXVIII) (commerciallyavailable from Ark Pharma Scientific Limited) (80 mg, 0.66 mmol),BrettPhos Pd G3 (50 mg, 0.06 mmol), and Cs₂CO₃ (360 mg, 1.1 mmol) in1,4-dioxane (5 mL) was purged with N₂ gas for 5 min. The mixture wasstirred at 110° C. for12 h. The reaction mixture was cooled to roomtemperature, filtered, and concentrated. The crude product was purifiedby silica gel chromatography (0→15% MeOH/CHCl₃) to afford tert-butyl3-oxo-6-[6-(pyridine-4-carbonylamino)-1H-pyrrolo[2,3-b]pyridin-3-yl]spiro[2H-indene-1,4′-piperidine]-1′-carboxylate(CLXXIX) (75 mg, 0.140 mmol, 26.1% yield) as a beige solid. ESIMS foundfor C₃₁H₃₁N₅O₄ m/z 538.1 (M+H).

Step 4

To a solution of tert-butyl3-oxo-6-[6-(pyridine-4-carbonylamino)-1H-pyrrolo[2,3-b]pyridin-3-yl]spiro[2H-indene-1,4′-piperidine]-1′-carboxylate(CLXXIX) (75 mg, 0.14 mmol) in DCM (5 mL) was added TFA (0.2 mL, 2.6mmol). The reaction mixture was stirred at room temperature for 5 h.Reaction mixture was concentrated, and the residue was purified bycolumn chromatography (0→10% 7 N NH₃ in MeOH/CHCl₃). The pure fractionswere combined and concentrated, resulting solids were triturated withDCM, filtered, and dried to giveN-(3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide(1898) (42 mg, 0.096 mmol, 68.8% yield) as a beige solid. ¹H NMR (499MHz, DMSO-d₆) δ ppm 1.46 (2H, br d, J=12.32 Hz), 2.07 (2H, td, J=12.73,4.11 Hz), 2.64 (2H, s), 2.70 (2H, br t, J=11.77 Hz), 3.02 (2H, br d,J=11.77 Hz), 7.65 (1H, d, J=7.94 Hz), 7.85 (1H, dd, J=8.08, 1.23 Hz),7.93-7.95 (2H, m), 7.96 (1H, s), 8.05 (1H, d, J=8.76 Hz), 8.11 (1H, s),8.45 (1H, d, J=8.49 Hz), 8.75-8.80 (2H, m), 11.03 (1H, br s), 12.03 (1H,br s); ESIMS found for C₂₆H₂₃N₅O₂ m/z 438.1 (M+1).

Step 5

A mixture ofN-[3-(1-oxospiro[2H-indene-3,4′-piperidine]-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl]pyridine-4-carboxamide(1898) (37 mg, 0.08 mmol), formaldehyde (30 μL, 0.38 mmol) and TEA (40μL, 0.29 mmol) in DCE (3 mL) and MeOH (1 mL) was stirred for 30 min atroom temperature. NaH(OAc)₃ (90 mg, 0.42 mmol) was then added and themixture was stirred at 37° C. for 5 h. The reaction mixture wasconcentrated, and the resulting residue was adsorbed on silica gel andpurified by column chromatography (0→10% MeOH/CHCl₃). Pure fractionswere collected and further purified by Preparative TLC (20% MeOH/CHCl₃)to produceN-(3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide(1899) (18 mg, 0.040 mmol, 47.1% yield) as a beige solid. ¹H NMR (499MHz, DMSO-d₆) δ ppm 1.50 (2H, br d, J=12.05 Hz), 2.01-2.09 (2H, m), 2.20(2H, br dd, J=12.87, 3.56 Hz), 2.24 (3H, s), 2.58 (2H, s), 2.83 (2H, brd, J=11.50 Hz), 7.65 (1H, d, J=7.94 Hz), 7.86 (1H, dd, J=7.94, 1.37 Hz),7.93-7.95 (2H, m), 8.00 (1H, s), 8.04 (1H, d, J=8.76 Hz), 8.13 (1H, d,J=2.46 Hz), 8.47 (1H, d, J=8.76 Hz), 8.76-8.79 (2H, m), 11.02 (1H, s),12.02 (1H, br s); ESIMS found for C₂₇H₂₅N₅O₂ m/z 452.1 (M+1).

The following compounds were prepared in accordance with the proceduresdescribed in the above Schemes 1-29.

1H,1′H-3,4′-Bipyrrolo[2,3-b]pyridine 2

Beige solid (8 mg, 0.034 mmol, 16.7% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 6.67 (1H, dd, J=3.57, 1.92 Hz), 7.20 (1H, dd, J=7.82, 4.53 Hz), 7.33(1H, d, J=4.94 Hz), 7.45-7.52 (1H, m), 8.04 (1H, s), 8.24-8.28 (2H, m),8.33 (1H, dd, J=4.67, 1.37 Hz), 11.67 (1H, br s); ESIMS found forC₁₄H₁₀N₄ m/z 235.0 (M+1).

2-Methyl-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole 3

Dark yellow solid (35.0 mg, 0.141 mmol, 34.4% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 4.18 (3H, s), 7.16 (1H, dd, J=7.82, 4.53 Hz), 7.59-7.68(2H, m), 7.84 (1H, d, J=2.47 Hz), 7.98 (1H, s), 8.27 (1H, dd, J=4.67,1.37 Hz), 8.30 (1H, s), 8.33 (1H, dd, J=7.96, 1.10 Hz), 11.82 (1H, brs); ESIMS found for C₁₅H₁₂N₄ m/z 249.0 (M+1).

2-(1H-Pyrrolo[2,3-b]pyridin-3-yl)thiazolo[5,4-b]pyridine 4

Beige solid (20 mg, 0.079 mmol, 51.9% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 7.33 (1H, dd, J=7.96, 4.67 Hz), 7.55 (1H, dd, J=7.96, 4.67 Hz),8.32 (1H, dd, J=8.10, 1.51 Hz), 8.39 (1H, dd, J=4.67, 1.65 Hz), 8.50(1H, s), 8.52 (1H, dd, J=4.67, 1.37 Hz), 8.71 (1H, dd, J=7.96, 1.65 Hz),12.61 (1H, br s); ESIMS found for C₁₃H₈N₄S m/z 253.0 (M+1).

2-(1H-Pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine 5

Yellow solid (30 mg, 0.119 mmol, 46.7% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 7.28 (1H, dd, J=8.10, 4.53 Hz), 7.74 (1H, dd, J=5.35, 0.96 Hz),7.82 (1H, s), 8.18 (1H, s), 8.36 (1H, dd, J=4.67, 1.37 Hz), 8.43 (1H, d,J=5.21 Hz), 8.46 (1H, dd, J=7.96, 1.37 Hz), 9.15 (1H, s), 12.32 (1H, brs); ESIMS found for C₁₄H₉N₃S m/z 252.1 (M+1).

2-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one8

Off-white solid (6.1 mg, 0.024 mmol, 17.5% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 3.61-3.69 (2H, m), 4.32-4.38 (2H, m), 7.12 (1H, s), 7.14(1H, dd, J=7.82, 4.53 Hz), 7.97 (1H, d, J=2.47 Hz), 8.19 (1H, br s),8.26 (1H, dd, J=4.67, 1.37 Hz), 8.47 (1H, dd, J=7.96, 1.65 Hz), 11.82(1H, br s); ESIMS found for C₁₃H₁₁N₅O m/z 254.1 (M+1).

6,6-Dimethyl-2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydro-4H-imidazo[1,5-b]pyrazol-4-one9

Beige solid (3 mg, 0.011 mmol, 13.1% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.70 (6H, s), 6.94 (1H, s), 7.16 (1H, dd, J=7.96, 4.67 Hz), 7.97(1H, d, J=2.47 Hz), 8.27 (1H, dd, J=4.67, 1.65 Hz), 8.49 (1H, dd,J=7.96, 1.37 Hz), 9.43 (1H, s), 11.86 (1H, br s); ESIMS found forC₁₄H₁₃N₅O m/z 268.1 (M+1).

7-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one10

Beige solid (20 mg, 0.079 mmol, 19.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.53 (2H, br t, J=7.14 Hz), 4.10-4.15 (2H, m), 6.99 (1H, d, J=1.65Hz), 7.10 (1H, dd, J=7.96, 4.67 Hz), 7.45 (1H, d, J=1.65 Hz), 7.65 (1H,br s), 7.68 (1H, d, J=2.47 Hz), 8.20 (1H, d, J=7.96 Hz), 8.22 (1H, dd,J=4.67, 1.37 Hz), 11.59 (1H, br s); ESIMS found for C₁₄H₁₂N₄O m/z 253.1(M+1).

2-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one11

Beige solid (20 mg, 0.074 mmol, 18.1% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.01 (2H, br t, J=6.59 Hz), 3.48 (2H, br t, J=5.35 Hz), 7.19 (1H,br dd, J=7.96, 4.67 Hz), 7.43 (1H, s), 7.58 (1H, br s), 7.90 (1H, br s),8.21 (1H, br d, J=7.96 Hz), 8.29 (1H, br d, J=3.84 Hz), 12.00 (1H, brs); ESIMS found for C₁₄H₁₁N₃OS m/z 270.0 (M+1).

6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine 12

Yellow solid (16 mg, 0.068 mmol, 30.1% yield). ¹HNMR (500 MHz, DMSO-d₆)δ ppm 7.20 (1H, dd, J=8.10, 4.53 Hz), 7.56 (1H, d, J=1.10 Hz), 7.60-7.69(2H, m), 7.97 (1H, s), 7.99 (1H, s), 8.31 (1H, dd, J=4.67, 1.37 Hz),8.41 (1H, dd, J=7.96, 1.37 Hz), 8.95 (1H, s), 11.98 (1H, br s); ESIMSfound for C₁₄H₁₀N₄ m/z 235.1 (M+1).

8-Fluoro-2-methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine13

Grey solid (12.5 mg, 0.047 mmol, 10.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 2.37 (3H, s), 7.20 (1H, dd, J=7.96, 4.39 Hz), 7.54 (1H, dd,J=12.62, 1.37 Hz), 7.80-7.87 (1H, m), 8.01 (1H, d, J=2.47 Hz), 8.31 (1H,dd, J=4.67, 1.65 Hz), 8.42 (1H, dd, J=7.96, 1.37 Hz), 8.76 (1H, d,J=1.37 Hz), 12.01 (1H, br s); ESIMS found for C₁₅H₁₁FN₄ m/z 267.0 (M+1).

N-(1-Methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide14

White solid (46 mg, 0.123 mmol, 27.6% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.60 (2H, qd, J=12.05, 3.83 Hz), 1.78-1.86 (2H, m), 1.92-2.02 (2H,m), 2.18 (3H, s), 2.80 (2H, br d, J=11.77 Hz), 3.78-3.90 (1H, m), 7.27(1H, dd, J=7.94, 4.65 Hz), 7.76 (1H, d, J=9.31 Hz), 7.88 (1H, dd,J=9.31, 1.92 Hz), 8.07 (1H, d, J=2.74 Hz), 8.26 (1H, br d, J=1.37 Hz),8.27 (1H, dd, J=4.52, 3.15 Hz), 8.33 (1H, dd, J=4.65, 1.37 Hz), 8.38(1H, s), 9.94 (1H, s), 12.08 (1H, br s); ESIMS found for C₂₁H₂₂N₆O m/z375.2 (M+1).

1-(6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)-N,N-dimethylmethanamine18

Beige solid (35 mg, 0.120 mmol, 69.1% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 2.21 (6H, s), 3.82 (2H, s), 7.21 (1H, dd, J=7.96, 4.67 Hz), 7.48(1H, s), 7.59-7.68 (2H, m), 7.97 (1H, d, J=2.47 Hz), 8.29 (1H, d, J=7.96Hz), 8.30-8.32 (1H, m), 8.68 (1H, s), 12.00 (1H, br s); ESIMS found forC₁₇H₁₇N₅ m/z 292.05 (M+1).

6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrazine 20

Beige solid (40 mg, 0.170 mmol, 63.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 7.21 (1H, dd, J=8.08, 4.52 Hz), 7.81 (1H, d, J=0.82 Hz), 8.09 (1H,s), 8.12 (1H, s), 8.31 (1H, dd, J=4.52, 1.51 Hz), 8.60 (1H, dd, J=7.94,1.64 Hz), 9.08 (1H, d, J=1.37 Hz), 9.13 (1H, d, J=0.82 Hz), 12.02 (1H,br s); ESIMS found for C₁₃H₉N₅ m/z 236.1 (M+1).

(6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrazin-3-yl)(4-methylpiperazin-1-yl)methanone21

Beige solid (7 mg, 0.019 mmol, 3.9% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 2.23 (3H, s), 2.42 (4H, t, J=4.93 Hz), 3.78 (4H, br s), 7.26 (1H,dd, J=7.94, 4.65 Hz), 8.17 (1H, s), 8.19 (1H, s), 8.26 (1H, dd, J=8.08,1.51 Hz), 8.35 (1H, dd, J=4.65, 1.37 Hz), 9.14 (1H, d, J=2.46 Hz), 9.51(1H, d, J=2.46 Hz), 12.20 (1H, br s); ESIMS found for C₁₉H₁₉N₇O m/z362.15 (M+1).

4-Fluoro-2-methyl-1-(piperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole23

White solid (45 mg, 0.129 mmol, 52.6% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.81 (2H, br d, J=9.61 Hz), 2.27 (2H, qd, J=12.17, 3.84 Hz), 2.61(3H, s), 2.63-2.72 (2H, m), 3.11 (2H, br d, J=12.08 Hz), 4.37-4.48 (1H,m), 7.19 (1H, dd, J=7.96, 4.67 Hz), 7.27 (1H, d, J=12.08 Hz), 7.71 (1H,d, J=1.10 Hz), 7.91 (1H, d, J=1.92 Hz), 8.24 (1H, dd, J=7.96, 1.37 Hz),8.29 (1H, dd, J=4.53, 1.51 Hz), 11.94 (1H, br s); ESIMS found forC₂₀H₂₀FN₅ m/z 350.15 (M+1).

4-Fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole24

Beige solid (25 mg, 0.069 mmol, 22.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.87 (2H, br d, J=10.15 Hz), 2.11-2.20 (2H, m), 2.25 (3H, s), 2.43(2H, qd, J=12.35, 3.57 Hz), 2.61 (3H, s), 2.95 (2H, br d, J=11.80 Hz),4.33 (1H, tt, J=12.28, 4.19 Hz), 7.19 (1H, dd, J=7.96, 4.67 Hz), 7.27(1H, dd, J=12.08, 0.82 Hz), 7.61 (1H, d, J=1.10 Hz), 7.93 (1H, d, J=1.92Hz), 8.22 (1H, dd, J=7.96, 1.37 Hz), 8.29 (1H, dd, J=4.53, 1.51 Hz),11.94 (1H, br s); ESIMS found for C₂₁H₂₂FN₅ m/z 364.2 (M+1).

1-Isopropyl-2-methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine25

Beige solid (36 mg, 0.124 mmol, 55.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.62 (6H, d, J=6.86 Hz), 2.63 (3H, s), 4.82 (1H, spt, J=6.86 Hz),7.19 (1H, dd, J=7.96, 4.67 Hz), 7.99 (1H, d, J=2.47 Hz), 8.21 (1H, d,J=1.92 Hz), 8.27 (1H, dd, J=7.96, 1.37 Hz), 8.30 (1H, dd, J=4.67, 1.65Hz), 8.67 (1H, d, J=1.92 Hz), 11.97 (1H, br s); ESIMS found for C₁₇H₁₇N₅m/z 292.15 (M+1).

3-Isopropyl-2-methyl-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3H-imidazo[4,5-b]pyridine 26

White solid (17 mg, 0.058 mmol, 19.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.63 (6H, d, J=6.86 Hz), 2.60 (3H, s), 4.79 (1H, spt, J=6.91 Hz),7.16 (1H, dd, J=7.96, 4.67 Hz), 8.03 (1H, d, J=1.10 Hz), 8.25 (1H, dd,J=4.67, 1.65 Hz), 8.30 (1H, d, J=2.74 Hz), 8.80 (1H, dd, J=7.96, 1.65Hz), 8.82 (1H, d, J=0.82 Hz), 11.88 (1H, br s); ESIMS found for C₁₇H₁₇N₅m/z 292.1 (M+1).

3-Isopropyl-2-methyl-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3H-imidazo[4,5-b]pyridine 27

White solid (35 mg, 0.120 mmol, 51.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.76 (6H, d, J=6.59 Hz), 2.60 (3H, s), 4.85 (1H, spt, J=6.91 Hz),7.22 (1H, dd, J=7.68, 4.67 Hz), 7.73 (1H, d, J=8.51 Hz), 7.87 (1H, d,J=8.51 Hz), 8.23 (1H, s), 8.29 (1H, dd, J=4.53, 1.51 Hz), 8.87 (1H, dd,J=7.68, 1.65 Hz), 11.98 (1H, br s); ESIMS found for C₁₇H₁₇N₅ m/z 292.15(M+1).

2-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-7,8-dihydro-6H-pyrrolo[2′,1′:2,3]imidazo[4,5-b]pyridine 28

White solid (46 mg, 0.167 mmol, 53.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 2.68 (2H, quin, J=7.34 Hz), 2.98-3.04 (2H, m), 4.24 (2H, t, J=7.00Hz), 7.19 (1H, dd, J=7.82, 4.53 Hz), 7.73 (1H, d, J=8.51 Hz), 7.90 (1H,d, J=8.51 Hz), 8.21 (1H, d, J=2.47 Hz), 8.28 (1H, dd, J=4.67, 1.65 Hz),8.91 (1H, dd, J=7.96, 1.65 Hz), 11.95 (1H, br s); ESIMS found forC₁₆H₁₃N₅ m/z 276.1 (M+1).

6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine 29

Light brown solid (20.0 mg, 0.085 mmol, 20.8% yield). ¹H NMR (500 MHz,DMSO-d₆) δ ppm 1.52-1.61 (4H, m), 1.62-1.70 (2H, m), 3.60-3.69 (4H, m),7.27 (1H, dd, J=7.96, 4.67 Hz), 7.47 (1H, dd, J=7.27, 2.06 Hz), 8.16(1H, d, J=1.37 Hz), 8.19 (1H, s), 8.22 (1H, d, J=2.74 Hz), 8.30-8.35(2H, m), 8.72-8.81 (1H, m), 12.21 (1H, br s); ESIMS found for C₁₃H₉N₅m/z 236.0 (M+1).

7-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine 30

Beige solid (25.0 mg, 0.106 mmol, 25.9% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 7.23 (1H, dd, J=7.96, 4.67 Hz), 7.64 (1H, dd, J=7.14,1.92 Hz), 8.10 (1H, d, J=1.37 Hz), 8.29 (1H, s), 8.33 (1H, dd, J=4.53,1.51 Hz), 8.45 (1H, s), 8.50 (1H, dd, J=7.96, 1.37 Hz), 8.93 (1H, d,J=7.14 Hz), 12.26 (1H, br s); ESIMS found for C₁₃H₉N₅ m/z 236.0 (M+1).

1-Methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole 31

Beige solid (60 mg, 0.241 mmol, 42.6% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 4.36 (3H, s), 7.22 (1H, dd, J=7.96, 4.67 Hz), 7.80 (1H, dd,J=8.64, 1.51 Hz), 8.05 (2H, d, J=8.51 Hz), 8.08 (1H, s), 8.32 (1H, dd,J=4.53, 1.51 Hz), 8.51 (1H, dd, J=7.96, 1.37 Hz), 12.05 (1H, br s);ESIMS found for C₁₄H₁₁N₅ m/z 250.05 (M+1).

3-Methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridine 32

Beige solid (35 mg, 0.140 mmol, 60.8% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 2.77 (3H, s), 7.21 (1H, dd, J=7.96, 4.67 Hz), 7.74-7.82 (2H, m),8.05 (1H, s), 8.32 (1H, dd, J=4.67, 1.65 Hz), 8.42 (1H, dd, J=7.96, 1.37Hz), 8.47 (1H, t, J=1.23 Hz), 12.07 (1H, br s); ESIMS found for C₁₄H₁₁N₅m/z 250.1 (M+1).

3-Methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine 34

Beige solid (5 mg, 0.020 mmol, 10.3% yield). ¹H NMR (500 MHz, DMSO-d₆) δppm 2.63 (3H, s), 7.28 (1H, dd, J=7.96, 4.67 Hz), 7.52 (1H, d, J=0.82Hz), 7.78 (1H, d, J=9.61 Hz), 8.04 (1H, d, J=9.61 Hz), 8.35 (1H, dd,J=4.67, 1.65 Hz), 8.49 (1H, s), 8.84 (1H, dd, J=7.96, 1.65 Hz), 12.27(1H, br s); ESIMS found for C₁₄H₁₁N₅ m/z 250.1 (M+1).

(6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazin-3-yl) methanol35

Light rose solid (12 mg, 0.045 mmol, 61.1% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 4.96 (2H, d, J=3.29 Hz), 5.29 (1H, br s), 7.27 (1H, dd,J=7.96, 4.67 Hz), 7.64 (1H, s), 7.82 (1H, d, J=9.61 Hz), 8.07 (1H, d,J=9.61 Hz), 8.34 (1H, dd, J=4.67, 1.65 Hz), 8.50 (1H, s), 8.86 (1H, dd,J=7.96, 1.65 Hz), 12.27 (1H, br s); ESIMS found for C₁₄H₁₁N₅O m/z 266.0(M+1).

3-(Pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine 36

Dark yellow solid (13 mg, 0.056 mmol, 51.9% yield). ¹H NMR (500 MHz,DMSO-d₆) δ ppm 6.58 (1H, d, J=2.20 Hz), 7.21 (1H, dd, J=7.96, 4.67 Hz),7.30 (1H, dd, J=7.41, 1.92 Hz), 7.96 (1H, d, J=2.20 Hz), 8.03 (1H, d,J=1.37 Hz), 8.12 (1H, s), 8.31 (1H, dd, J=4.53, 1.51 Hz), 8.47 (1H, dd,J=7.96, 1.65 Hz), 8.67 (1H, d, J=7.41 Hz), 12.08 (1H, br s); ESIMS foundfor C₁₄H₁₀N₄ m/z 235.1 (M+1).

3-(3-(1-Methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine37

Light orange solid (12 mg, 0.038 mmol, 24.8% yield). ¹H NMR (500 MHz,DMSO-d₆) δ ppm 3.92 (3H, s), 7.24 (1H, dd, J=7.96, 4.67 Hz), 7.31 (1H,dd, J=7.14, 1.92 Hz), 7.89 (1H, s), 7.96 (1H, dd, J=1.92, 0.82 Hz), 8.18(3H, s), 8.32 (1H, dd, J=4.67, 1.65 Hz), 8.39 (1H, dd, J=7.96, 0.82 Hz),8.68 (1H, dd, J=7.14, 0.82 Hz), 12.13 (1H, br s); ESIMS found forC₁₈H₁₄N₆ m/z 315.05 (M+1).

3-(3-(Pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine 38

Light yellow solid (14 mg, 0.045 mmol, 33.8% yield). ¹H NMR (500 MHz,DMSO-d₆) δ ppm 7.24 (1H, dd, J=7.96, 4.67 Hz), 7.42 (1H, dd, J=7.41,1.92 Hz), 7.50 (1H, ddd, J=7.96, 4.67, 0.82 Hz), 8.13 (1H, dd, J=1.92,0.82 Hz), 8.18 (1H, ddd, J=7.96, 2.47, 1.65 Hz), 8.24 (1H, d, J=2.47Hz), 8.32 (1H, dd, J=4.67, 1.37 Hz), 8.38 (1H, dd, J=8.10, 1.51 Hz),8.46 (1H, s), 8.49 (1H, dd, J=4.67, 1.65 Hz), 8.75-8.83 (1H, m), 9.01(1H, dd, J=2.47, 0.82 Hz), 12.17 (1H, br s); ESIMS found for C₁₉H₁₃N₅m/z 312.1 (M+1).

N-((3-Fluoroazetidin-3-yl)methyl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide 41

Light brown solid (47 mg, 0.129 mmol, 55.5% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 3.49-3.64 (4H, m), 3.80 (2H, dd, J=23.30, 6.00 Hz), 7.29(1H, dd, J=7.80, 4.79 Hz), 7.50 (1H, dd, J=7.39, 1.92 Hz), 8.24 (1H, s),8.34-8.37 (1H, m), 8.39 (1H, brt, J=6.02 Hz), 8.57 (1H, d, J=1.37 Hz),8.61 (1H, s), 8.76 (1H, d, J=7.39 Hz), 12.23 (1H, br s); ESIMS found forC₁₉H₁₇FN₆O m/z 365.15 (M+1).

N-((3-Fluoro-1-methylazetidin-3-yl)methyl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide 42

Beige solid (5 mg, 0.013 mmol, 10.2% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 2.29 (3H, s), 3.00-3.11 (2H, m), 3.46-3.56 (2H, m), 3.76 (2H, dd,J=23.30, 6.30 Hz), 7.29 (1H, dd, J=7.80, 4.79 Hz), 7.50 (1H, dd, J=7.26,2.05 Hz), 8.24 (1H, d, J=2.74 Hz), 8.33-8.37 (2H, m), 8.39-8.43 (1H, m),8.56 (1H, d, J=1.37 Hz), 8.61 (1H, s), 8.75-8.78 (1H, m), 12.23 (1H, brs); ESIMS found for C₂₀H₁₉FN₆O m/z 379.2 (M+1).

N-((3R,4R)-3-Fluoropiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide 43

Beige solid (123 mg, 0.325 mmol, 59.6% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.46 (1H, qd, J=12.14, 4.11 Hz), 1.83-1.92 (1H, m), 2.43-2.49 (2H,m), 2.83-2.91 (1H, m), 3.22-3.29 (1H, m), 4.03-4.15 (1H, m), 4.43 (1H,dtd, J=50.45, 9.58, 9.58, 4.65 Hz), 7.26-7.33 (1H, m), 7.49 (1H, dd,J=7.26, 2.05 Hz), 8.20 (1H, d, J=8.49 Hz), 8.24 (1H, d, J=2.46 Hz), 8.34(1H, s), 8.35-8.37 (1H, m), 8.55 (1H, s), 8.57 (1H, d, J=1.64 Hz), 8.75(1H, d, J=7.39 Hz), 12.22 (1H, br s); ESIMS found for C₂₀H₁₉FN₆O m/z379.2 (M+1).

N-((3R,4R)-3-Fluoro-1-methylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide 44

Off-white solid (7 mg, 0.018 mmol, 13.5% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.52-1.65 (1H, m), 1.83-1.93 (1H, m), 1.97-2.08 (2H, m),2.25 (3H, s), 2.69-2.77 (1H, m), 3.10-3.19 (1H, m), 3.94-4.08 (1H, m),4.57(1H, dtd, J=49.90, 9.65, 9.65, 4.79 Hz), 7.28-7.31 (1H, m), 7.50(1H, dd, J=7.26, 2.05 Hz), 8.19 (1H, d, J=8.49 Hz), 8.24 (1H, d, J=1.92Hz), 8.34 (1H, s), 8.35-8.37 (1H, m), 8.53 (1H, s), 8.57 (1H, d, J=1.37Hz), 8.72-8.80 (1H, m), 12.23 (1H, br s); ESIMS found for C₂₁H₂₁FN₆O m/z393.2 (M+1).

N-(1-Methylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide 45

Grey solid (22.0 mg, 0.059 mmol, 14.3% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 1.58 (2H, qd, J=11.98, 3.84 Hz), 1.75-1.85 (2H, m), 1.96 (2H, td,J=11.87, 2.06 Hz), 2.18 (3H, s), 2.80 (2H, br d, J=11.80 Hz), 3.73-3.87(1H, m), 7.25-7.33(1H, m), 7.47(1H, dd, J=7.41, 2.20 Hz), 7.95 (1H, d,J=7.68 Hz), 8.23 (1H, d, J=2.74 Hz), 8.34 (1H, s), 8.35-8.38 (1H, m),8.56 (1H, s), 8.56-8.58 (1H, m), 8.70-8.77 (1H, m), 12.22 (1H, br s);ESIMS found for C₂₁H₂₂N₆O m/z 375.1 (M+1).

N-Methyl-N-(1-methylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide46

Amber solid (55 mg, 0.142 mmol, 34.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.64 (2H, br d, J=10.13 Hz), 1.85 (2H, qd, J=12.00, 3.42 Hz),1.92-2.01 (2H, m), 2.17 (3H, s), 2.85 (2H, br d, J=11.50 Hz), 3.05 (3H,br s), 4.17-4.31 (1H, m), 7.28 (1H, dd, J=7.94, 4.65 Hz), 7.49 (1H, dd,J=7.26, 2.05 Hz), 8.22 (1H, d, J=2.46 Hz), 8.25 (1H, s), 8.30-8.32 (2H,m), 8.34 (1H, dd, J=4.65, 1.64 Hz), 8.74-8.80 (1H, m), 12.21 (1H, br s);ESIMS found for C₂₂H₂₄N₆O m/z 389.2 (M+1).

N-(1-Cyclopropylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide 47

Off-white solid (21.0 mg, 0.052 mmol, 20.1% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 0.26-0.34 (2H, m), 0.39-0.46 (2H, m), 1.48 (2H, qd,J=11.91, 3.70 Hz), 1.61 (1H, tt, J=6.71, 3.42 Hz), 1.78-1.86 (2H, m),2.24 (2H, td, J=11.77, 2.19 Hz), 2.96 (2H, br d, J=11.77 Hz), 3.76-3.89(1H, m), 7.26-7.33 (1H, m), 7.47 (1H, dd, J=7.26, 2.05 Hz), 7.92 (1H, d,J=7.67 Hz), 8.23 (1H, s), 8.34 (1H, s), 8.35 (1H, q, J=1.46 Hz), 8.54(1H, s), 8.56-8.57 (1H, m), 8.70-8.78 (1H, m), 12.22 (1H, s); ESIMSfound for C₂₃H₂₄N₆O m/z 401.1 (M+1).

N-(1-(cyclopropylmethyl)piperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide48

Beige solid (92 mg, 0.222 mmol, 53.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 0.04-0.11(2H, m), 0.42-0.50 (2H, m), 0.77-0.89 (1H, m), 1.57 (2H,qd, J=11.91, 3.70 Hz), 1.78-1.88 (2H, m), 1.94-2.06 (2H, m), 2.18 (2H,d, J=6.57 Hz), 3.00 (2H, br d, J=11.77 Hz), 3.75-3.86 (1H, m), 7.27-7.32(1H, m), 7.47 (1H, dd, J=7.26, 2.05 Hz), 7.96 (1H, d, J=7.67 Hz), 8.23(1H, s), 8.34 (1H, s), 8.35-8.36 (1H, m), 8.56 (1H, s), 8.57 (1H, d,J=1.64 Hz), 8.74 (1H, d, J=7.39 Hz), 12.22 (1H, br s); ESIMS found forC₂₄H₂₆N₆O m/z 415.2 (M+1).

N-(1-(2,2-Difluoropropyl)piperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide49

Grey solid (45 mg, 0.103 mmol, 24.8% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.54-1.63 (2H, m), 1.63 (3H, br t, J=19.03 Hz), 1.78-1.85 (2H, m),2.25-2.35 (2H, m), 2.73 (2H, t, J=14.10 Hz), 2.93 (2H, br d, J=12.05Hz), 3.76-3.87 (1H, m), 7.25-7.32 (1H, m), 7.48 (1H, dd, J=7.39, 2.19Hz), 7.95 (1H, d, J=7.94 Hz), 8.23 (1H, s), 8.34 (1H, s), 8.35 (1H, s),8.55 (1H, s), 8.57 (1H, d, J=1.37 Hz), 8.74 (1H, d, J=7.39 Hz), 12.22(1H, br s); ESIMS found for C₂₃H₂₄F₂N₆O m/z 439.2 (M+1).

N-(1-(2-Methoxyethyl)piperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide50

White solid (42 mg, 0.100 mmol, 24.6% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.55 (2H, qd, J=11.96, 3.56 Hz), 1.81 (2H, br d, J=9.86 Hz),2.00-2.11 (2H, m), 2.48 (2H, t, J=6.05 Hz), 2.91 (2H, br d, J=11.77 Hz),3.24 (3H, s), 3.44 (2H, t, J=5.89 Hz), 3.74-3.86 (1H, m), 7.26-7.32 (1H,m), 7.47 (1H, dd, J=7.26, 2.05 Hz), 7.94 (1H, d, J=7.67 Hz), 8.23 (1H,s), 8.34 (1H, s), 8.35 (1H, d, J=1.10 Hz), 8.55 (1H, s), 8.56 (1H, d,J=1.64 Hz), 8.74 (1H, d, J=7.12 Hz), 12.22 (1H, br s); ESIMS found forC₂₃H₂₆N₆O₂ m/z 419.2 (M+1).

N-(1-(Pyridin-2-ylmethyl)piperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide51

White solid (36 mg, 0.080 mmol, 22.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.61 (2H, qd, J=11.96, 3.83 Hz), 1.80-1.89 (2H, m), 2.08-2.19 (2H,m), 2.87 (2H, br d, J=11.77 Hz), 3.61 (2H, s), 3.79-3.91 (1H, m),7.25-7.31 (2H, m), 7.45 (1H, d, J=7.67 Hz), 7.48 (1H, dd, J=7.26, 2.05Hz), 7.78 (1H, td, J=7.67, 1.92 Hz), 7.97 (1H, d, J=7.94 Hz), 8.23 (1H,d, J=2.46 Hz), 8.34 (1H, s), 8.35 (1H, s), 8.47-8.52 (1H, m), 8.56 (1H,s), 8.57 (1H, d, J=1.37 Hz), 8.74 (1H, d, J=7.39 Hz), 12.22 (1H, br s);ESIMS found for C₂₆H₂₅N₇O m/z 452.2 (M+1).

N-(Pyridin-3-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide52

Brown solid (5.0 mg, 0.014 mmol, 5.3% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 7.31 (1H, dd, J=7.96, 4.67 Hz), 7.40 (1H, dd, J=8.23, 4.39 Hz),7.54-7.55 (1H, m), 7.57 (1H, dd, J=7.27, 2.06 Hz), 8.23 (1H, ddd,J=8.37, 2.47, 1.51 Hz), 8.27-8.32 (2H, m), 8.36 (1H, dd, J=4.67, 1.65Hz), 8.38 (1H, dd, J=8.10, 1.51 Hz), 8.60 (1H, d, J=1.37 Hz), 8.77 (1H,s), 8.84 (1H, d, J=7.14 Hz), 8.93 (1H, d, J=2.47 Hz), 10.12 (1H, s),12.27 (1H, br s); ESIMS found for C₂₀H₁₄N₆O m/z 355.1 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone 53

Tan solid (28.0 mg, 0.081 mmol, 20.8% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 1.52-1.61 (4H, m), 1.62-1.70 (2H, m), 3.60-3.69 (4H, m), 7.27 (1H,dd, J=7.96, 4.67 Hz), 7.47 (1H, dd, J=7.27, 2.06 Hz), 8.16 (1H, d,J=1.37 Hz), 8.19 (1H, s), 8.22 (1H, d, J=2.74 Hz), 8.30-8.35 (2H, m),8.72-8.81 (1H, m), 12.21 (1H, br s); ESIMS found for C₂₀H₁₉N₅O m/z 346.1(M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-(4-methylpiperazin-1-yl)piperidin-1-yl)methanone54

Beige solid (6 mg, 0.014 mmol, 4.9% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.36-1.50 (2H, m), 1.83 (2H, br d, J=11.23 Hz), 2.13 (3H, s),2.21-2.38 (4H, m), 2.41-2.49 (4H, m), 2.90-3.11 (3H, m), 4.28-4.40 (2H,m), 7.26 (1H, dd, J=7.80, 4.79 Hz), 7.48 (1H, dd, J=7.39, 1.92 Hz), 8.15(1H, d, J=1.37 Hz), 8.21-8.24 (2H, m), 8.31-8.35 (2H, m), 8.77 (1H, d,J=7.12 Hz), 12.22 (1H, br s); ESIMS found for C₂₅H₂₉N₇O m/z 444.3 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone55

Yellow solid (52.5 mg, 0.146 mmol, 47.3% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.22 (3H, s), 2.38 (4H, t, J=5.08 Hz), 3.66-3.72 (4H, m),7.28 (1H, dd, J=7.82, 4.80 Hz), 7.49 (1H, dd, J=7.14, 1.92 Hz),8.15-8.20 (1H, m), 8.22-8.25 (2H, m), 8.32-8.34 (1H, m), 8.34 (1H, s),8.78 (1H, dd, J=7.41, 0.82 Hz), 12.22 (1H, br s); ESIMS found forC₂₀H₂₀N₆O m/z 361.1 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-cyclopropylpiperazin-1-yl)methanone56

Tan solid (25 mg, 0.065 mmol, 15.5% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 0.31-0.39 (2H, m), 0.41-0.49 (2H, m), 1.66 (1H, tt, J=6.61, 3.52Hz), 2.61 (4H, t, J=4.93 Hz), 3.62-3.69 (4H, m), 7.24-7.31 (1H, m), 7.49(1H, dd, J=7.26, 2.05 Hz), 8.18 (1H, d, J=1.64 Hz), 8.23-8.25 (2H, m),8.32-8.34 (1H, m), 8.34 (1H, s), 8.78 (1H, d, J=7.12 Hz), 12.22 (1H, brs); ESIMS found for C₂₂H₂₂N₆O m/z 387.2 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4,7-diazaspiro[2.5]octan-7-yl)methanone57

White solid (45 mg, 0.121 mmol, 73.2% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 0.45 (4H, s), 2.78-2.84 (2H, m), 3.53 (2H, s), 3.66 (2H, dd,J=5.63, 4.25 Hz), 7.27 (1H, dd, J=7.96, 4.67 Hz), 7.48 (1H, dd, J=7.27,2.06 Hz), 8.17 (1H, d, J=1.37 Hz), 8.20 (1H, s), 8.23 (1H, d, J=2.47Hz), 8.30-8.35 (2H, m), 8.76 (1H, d, J=7.14 Hz), 12.22 (1H, br s); ESIMSfound for C₂₁H₂₀N₆O m/z 373.1 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)methanone58

Off-white solid (10 mg, 0.026 mmol, 23.8% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.50 (2H, br d, J=3.56 Hz), 1.89 (2H, br d, J=4.65 Hz),2.19 (3H, s), 3.12 (2H, br s), 3.17-3.44 (2H, m), 3.92-4.17 (2H, m),7.28 (1H, dd, J=7.94, 4.65 Hz), 7.48 (1H, dd, J=7.39, 2.19 Hz),8.21-8.24 (3H, m), 8.31 (1H, dd, J=8.08, 1.51 Hz), 8.34 (1H, dd, J=4.65,1.64 Hz), 8.77 (1H, dd, J=7.12, 0.82 Hz), 12.22 (1H, br s); ESIMS foundfor C₂₂H₂₂N₆O m/z 387.1 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone59

Off-white solid (41.0 mg, 0.106 mmol, 24.7% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.79-1.85 (2H, m), 1.87 (2H, br d, J=7.67 Hz), 2.19 (3H,s), 2.25 (2H, br d, J=9.86 Hz), 2.73 (2H, dd, J=10.68, 1.92 Hz), 4.61(2H, br s), 7.28 (1H, dd, J=7.94, 4.65 Hz), 7.50 (1H, dd, J=7.26, 2.05Hz), 8.24 (1H, d, J=3.01 Hz), 8.32 (1H, s), 8.32-8.36 (3H, m), 8.79 (1H,d, J=7.39 Hz), 12.22 (1H, br s); ESIMS found for C₂₂H₂₂N₆O m/z 387.1(M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone 60

Tan solid (25.0 mg, 0.072 mmol, 18.5% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 3.64-3.69 (4H, m), 3.69-3.73 (4H, m), 7.24-7.32 (1H, m), 7.50 (1H,dd, J=7.27, 2.06 Hz), 8.20-8.22 (1H, m), 8.23 (1H, s), 8.28 (1H, s),8.32-8.34 (1H, m), 8.34 (1H, s), 8.78 (1H, dd, J=7.41, 0.82 Hz), 12.22(1H, br s); ESIMS found for C₁₉H₁₇N₅O₂ m/z 348.1 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(2,6-diazaspiro[3.3]heptan-2-yl)methanone61

Beige solid (18 mg, 0.050 mmol, 41.1% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.62 (4H, s), 4.04-4.25 (2H, m), 4.45-4.64 (2H, m), 7.29 (1H, dd,J=7.94, 4.65 Hz), 7.53 (1H, dd, J=7.26, 2.05 Hz), 8.25 (1H, s), 8.27(1H, s), 8.31-8.36 (2H, m), 8.57 (1H, d, J=1.37 Hz), 8.76-8.82 (1H, m),12.19 (1H, br s); ESIMS found for C₂₀H₁₈N₆O m/z 359.2 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(6-methyl-2,6-diazaspiro[3.3]heptan-2-yl)methanone62

Off-white solid (11 mg, 0.030 mmol, 70.6% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.18 (3H, s), 3.27 (4H, s), 4.11 (2H, br s), 4.54 (2H, brs), 7.29 (1H, br dd, J=7.94, 4.65 Hz), 7.53 (1H, dd, J=7.39, 2.19 Hz),8.25 (1H, d, J=2.46 Hz), 8.26 (1H, s), 8.31-8.36 (2H, m), 8.57 (1H, d,J=1.37 Hz), 8.79 (1H, d, J=7.12 Hz), 12.24 (1H, br s); ESIMS found forC₂₁H₂₀N₆O m/z 373.2 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone 63

Light brown solid (47 mg, 0.126 mmol, 70.2% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.66 (1H, d, J=3.01 Hz), 2.68 (1H, d, J=3.01 Hz), 2.80(2H, br s), 2.91 (2H, br dd, J=10.95, 7.12 Hz), 3.49-3.60 (2H, m),3.89-4.03 (2H, m), 7.29 (1H, dd, J=7.80, 4.79 Hz), 7.51 (1H, dd, J=7.26,2.05 Hz), 8.23 (1H, s), 8.32-8.34 (1H, m), 8.35 (1H, s), 8.37 (1H, s),8.55 (1H, d, J=1.64 Hz), 8.77 (1H, d, J=7.12 Hz), 12.22 (1H, br s);ESIMS found for C₂₁H₂₀N₆O m/z 373.2 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone64

White solid (5 mg, 0.013 mmol, 10.3% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 2.22 (3H, s), 2.38-2.46 (2H, m), 2.53 (2H, dd, J=9.03, 1.92 Hz),2.87 (2H, br s), 3.58 (2H, br d, J=3.29 Hz), 3.97 (2H, br d, J=1.64 Hz),7.28 (1H, dd, J=7.80, 4.79 Hz), 7.51 (1H, dd, J=7.26, 2.05 Hz), 8.23(1H, d, J=2.74 Hz), 8.32-8.34 (1H, m), 8.34 (1H, s), 8.36 (1H, s),8.51-8.56 (1H, m), 8.77 (1H, dd, J=7.12, 0.82 Hz), 12.22 (1H, br s);ESIMS found for C₂₂H₂₂N₆O m/z 387.2 (M+1).

5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyrimidine 65

Beige solid (6.5 mg, 0.028 mmol, 94.3% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 6.61 (1H, dd, J=2.20, 0.82 Hz), 7.26 (1H, dd, J=7.96, 4.67 Hz),7.56 (1H, d, J=7.41 Hz), 8.11 (1H, d, J=2.47 Hz), 8.33 (1H, dd, J=4.67,1.65 Hz), 8.57 (1H, s), 8.92 (1H, dd, J=7.82, 1.78 Hz), 8.99 (1H, dd,J=7.41, 0.82 Hz), 12.33 (1H, br s); ESIMS found for C₂₂H₂₂N₆O m/z 236.1(M+1).

3-(4-Methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine 66

Beige solid (14 mg, 0.062 mmol, 28.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.79 (3H, s), 6.97-7.06 (2H, m), 7.13 (1H, dd, J=7.96, 4.67 Hz),7.60-7.67 (2H, m), 7.74 (1H, d, J=2.47 Hz), 8.22 (1H, dd, J=7.96, 1.37Hz), 8.25 (1H, dd, J=4.53, 1.51 Hz), 11.79 (1H, br s); ESIMS found forC₁₄H₁₂N₂O m/z 225.1 (M+1).

3-(6-Methoxypyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine 67

White solid (20 mg, 0.089 mmol, 59.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.89 (3H, s), 6.90 (1H, d, J=8.51 Hz), 7.14 (1H, dd, J=7.96, 4.67Hz), 7.86 (1H, d, J=2.47 Hz), 8.04 (1H, dd, J=8.51, 2.47 Hz), 8.25 (1H,dd, J=7.96, 1.37 Hz), 8.27 (1H, dd, J=4.67, 1.37 Hz), 8.53 (1H, d,J=2.47 Hz), 11.91(1H, br s); ESIMS found for C₁₃H₁₁N₃O m/z 226.1 (M+1).

3-(6-Methoxypyridazin-3-yl)-1H-pyrrolo[2,3-b]pyridine 69

White solid (33.5 mg, 0.148 mmol, 38.2% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 4.05 (3H, s), 7.21 (1H, dd, J=7.96, 4.67 Hz), 7.23 (1H,d, J=9.06 Hz), 8.14 (1H, d, J=9.33 Hz), 8.29-8.31 (1H, m), 8.30(1H, s),8.77(1H, dd, J=7.96, 1.65 Hz), 12.11 (1H, br s); ESIMS found forC₁₂H₁₀N₄O m/z 227.2 (M+1).

N-(1-Methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-amine70

Beige solid (42 mg, 0.136 mmol, 47.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.46-1.61 (2H, m), 2.01 (2H, br d, J=10.70 Hz), 2.10 (2H, br t,J=10.57 Hz), 2.22 (3H, s), 2.80 (2H, br d, J=11.53 Hz), 3.73-3.86 (1H,m), 6.91 (1H, d, J=7.14 Hz), 7.16 (1H, dd, J=7.96, 4.67 Hz), 7.68 (1H,s), 8.22 (1H, d, J=2.74 Hz), 8.23 (1H, s), 8.27 (1H, dd, J=4.67, 1.65Hz), 8.70 (1H, dd, J=7.96, 1.65 Hz), 12.05 (1H, br s); ESIMS found forC₁₇H₂₀N₆ m/z 309.1 (M+1).

3-(Pyridin-3-ylethynyl)-1H-pyrrolo[2,3-b]pyridine 71

Beige solid (35 mg, 0.160 mmol, 39.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 7.21 (1H, dd, J=7.96, 4.67 Hz), 7.45 (1H, ddd, J=7.89, 4.87, 0.96Hz), 7.95-7.99 (2H, m), 8.13 (1H, dd, J=7.68, 1.65 Hz), 8.33 (1H, dd,J=4.67, 1.37 Hz), 8.55 (1H, dd, J=4.80, 1.51 Hz), 8.74-8.79 (1H, m),12.23 (1H, br s); ESIMS found for C₁₄H₉N₃ m/z 220.0 (M+1).

3-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-1H-pyrrolo[2,3-b] pyridine72

Beige solid (50 mg, 0.189 mmol, 46.2% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.36 (6H, s), 4.24 (2H, s), 6.83 (1H, d, J=8.23 Hz), 7.13 (1H, dd,J=7.82, 4.53 Hz), 7.42 (1H, dd, J=8.23, 1.92 Hz), 7.50 (1H, d, J=1.92Hz), 7.71 (1H, s), 8.20 (1H, dd, J=7.96, 1.37 Hz), 8.25 (1H, dd, J=4.67,1.37 Hz), 11.76 (1H, br s); ESIMS found for C₁₇H₁₆N₂O m/z 265.1 (M+1).

2-Methyl-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one 76

White solid (20.1 mg, 0.076 mmol, 33.1% yield). ¹HNMR (499 MHz, DMSO-d₆)δ ppm 3.09 (3H, s), 4.51 (2H, s), 7.19 (1H, dd, J=7.96, 4.67 Hz), 7.69(1H, d, J=7.96 Hz), 7.84 (1H, dd, J=7.96, 1.10 Hz), 7.94 (1H, s), 8.02(1H, d, J=2.47 Hz), 8.30 (1H, dd, J=4.67, 1.37 Hz), 8.39 (1H, dd,J=7.96, 1.37 Hz), 12.04 (1H, br s); ESIMS found for C₁₆H₁₃N₃O m/z 264.1(M+1).

6′-(1H-Pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one78

White solid (4.2 mg, 0.013 mmol, 14.1% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.41 (3H, br d, J=12.90 Hz), 1.67-1.76 (5H, m), 2.00-2.11 (2H, m),7.20 (1H, dd, J=7.96, 4.67 Hz), 7.64 (1H, d, J=7.68 Hz), 7.80 (1H, dd,J=7.96, 1.37 Hz), 7.90 (1H, s), 8.03 (1H, d, J=2.74 Hz), 8.30 (1H, dd,J=4.67, 1.37 Hz), 8.36 (1H, dd, J=8.10, 1.24 Hz), 9.07 (1H, s), 12.05(1H, br s); ESIMS found for C₂₀H₁₉N₃O m/z 318.15 (M+1).

3-(Chroman-6-yl)-1H-pyrrolo[2,3-b]pyridine 79

White solid (50 mg, 0.200 mmol, 86.7% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.90-2.00(2H, m), 2.82(2H, t, J=6.45 Hz), 4.11-4.18 (2H, m),6.79(1H, d, J=8.78 Hz), 7.12 (1H, dd, J=7.96, 4.67 Hz), 7.36-7.40 (2H,m), 7.69 (1H, d, J=2.20 Hz), 8.21 (1H, dd, J=7.96, 1.37 Hz), 8.24 (1H,dd, J=4.53, 1.51 Hz), 11.74 (1H, br s); ESIMS found for C₁₆H₁₄N₂O m/z251.1 (M+1).

2,2-Dimethyl-7-(1H-pyrrolo[2,3-b]pyridin-3-yl)chroman-4-one 80

White solid (12 mg, 0.041 mmol, 20.9% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.44 (6H, s), 2.79 (2H, s), 7.19 (1H, dd, J=7.96, 4.67 Hz), 7.32(1H, d, J=1.65 Hz), 7.46 (1H, dd, J=8.23, 1.65 Hz), 7.77 (1H, d, J=8.23Hz), 8.12 (1H, s), 8.30 (1H, dd, J=4.67, 1.37 Hz), 8.34 (1H, dd, J=8.10,1.51 Hz), 12.15 (1H, br s); ESIMS found for C₁₈H₁₆N₂O₂ m/z 293.1 (M+1).

4,4-Dimethyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one82

Off-white solid (29 mg, 0.095 mmol, 69.2% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.35 (6H, s), 3.20 (2H, d, J=3.02 Hz), 7.19 (1H, dd,J=7.96, 4.67 Hz), 7.68-7.71 (2H, m), 7.89 (1H, br s), 7.89-7.92 (1H, m),8.04 (1H, d, J=2.20 Hz), 8.28-8.33 (2H, m), 12.05 (1H, br s); ESIMSfound for C₁₈H₁₇N₃O m/z 292.1 (M+1).

7-(1H-Pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one 83

Beige solid (74 mg, 0.222 mmol, 87.5% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.55-1.66 (2H, m), 1.84 (2H, br d, J=13.45 Hz), 2.69 (2H, dt,J=12.56, 4.15 Hz), 2.78 (2H, s), 2.84-2.94 (2H, m), 7.20 (1H, dd,J=7.96, 4.67 Hz), 7.36 (1H, d, J=1.65 Hz), 7.45 (1H, dd, J=8.23, 1.65Hz), 7.76 (1H, d, J=8.23 Hz), 8.13 (1H, s), 8.30 (1H, dd, J=4.67, 1.37Hz), 8.35 (1H, dd, J=7.96, 1.37 Hz), 12.16 (1H, br s); ESIMS found forC₂₀H₁₉N₃O₂ m/z 334.1 (M+1).

8-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one84

White solid (19 mg, 0.068 mmol, 46.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.34-3.41 (2H, m), 4.31-4.37 (2H, m), 7.18 (1H, dd, J=7.96, 4.67Hz), 7.35 (1H, d, J=1.65 Hz), 7.52 (1H, dd, J=8.23, 1.92 Hz), 7.86 (1H,d, J=8.23 Hz), 8.03 (1H, s), 8.26 (1H, br t, J=5.08 Hz), 8.29 (1H, dd,J=4.53, 1.51 Hz), 8.32 (1H, dd, J=8.10, 1.51 Hz), 12.05 (1H, br s);ESIMS found for C₁₆H₁₃N₃O₂ m/z 280.1 (M+1).

4-Methyl-8-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one 85

Beige solid (31 mg, 0.106 mmol, 75.1% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.10 (3H, s), 3.59 (2H, t, J=5.08 Hz), 4.41 (2H, t, J=4.94 Hz),7.18 (1H, dd, J=7.96, 4.67 Hz), 7.35 (1H, d, J=1.65 Hz), 7.54 (1H, dd,J=7.96, 1.65 Hz), 7.72 (1H, d, J=8.23 Hz), 8.02 (1H, d, J=2.74 Hz), 8.29(1H, dd, J=4.67, 1.37 Hz), 8.32 (1H, dd, J=7.96, 1.10 Hz), 12.04 (1H, brs); ESIMS found for C₁₇H₁₅N₃O₂ m/z 294.1 (M+1).

9-Fluoro-8-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one 86

White solid (18 mg, 0.061 mmol, 45.7% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.41 (2H, q, J=5.21 Hz), 4.39-4.45 (2H, m), 7.18 (1H, dd, J=8.10,4.53 Hz), 7.47 (1H, dd, J=8.37, 6.72 Hz), 7.64 (1H, dd, J=8.23, 1.37Hz), 7.84-7.91 (1H, m), 8.15 (1H, d, J=7.96 Hz), 8.31 (1H, dd, J=4.67,1.37 Hz), 8.41 (1H, br t, J=5.21 Hz), 12.16 (1H, br s); ESIMS found forC₁₆H₁₂FN₃O₂ m/z 298.1 (M+1).

6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)quinoline 87

Light brown solid (10 mg, 0.041 mmol, 8.0% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 7.23 (1H, dd, J=7.96, 4.67 Hz), 7.53 (1H, dd, J=8.37,4.25 Hz), 8.05 (1H, d, J=8.78 Hz), 8.11 (1H, s), 8.19 (1H, dd, J=8.78,2.20 Hz), 8.30-8.34 (2H, m), 8.41-8.47 (1H, m), 8.53 (1H, dd, J=7.96,1.37 Hz), 8.84 (1H, dd, J=4.12, 1.65 Hz), 12.06 (1H, br s); ESIMS foundfor C₁₆H₁₁N₃ m/z 246.1 (M+1).

(6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)quinolin-4-yl)(4,7-diazaspiro[2.5]octan-7-yl)methanone88

Beige solid (20 mg, 0.052 mmol, 50.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 0.01-0.20 (1H, m), 0.32 (1H, br dd, J=6.86, 5.21 Hz), 0.53 (1H, brs), 0.68 (1H, br s), 2.59-2.70 (1H, m), 2.94 (1H, br s), 3.16 (1H, brs), 3.38-3.50 (1H, m), 3.56-3.92 (2H, m), 7.19-7.27 (1H, m), 7.35-7.45(1H, m), 7.99-8.05 (1H, m), 8.07-8.16 (2H, m), 8.22 (1H, dd, J=8.78,1.92 Hz), 8.27-8.33 (1H, m), 8.34 (1H, dd, J=4.67, 1.37 Hz), 8.83-8.93(1H, m), 11.92 (1H, br s); ESIMS found for C₂₃H₂₁N₅O m/z 384.1 (M+1).

N-(1-Methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline-4-carboxamide 89

Yellow solid (20 mg, 0.052 mmol, 25.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.60 (2H, qd, J=11.76, 3.70 Hz), 1.85-1.95 (2H, m), 1.98-2.07 (2H,m), 2.17 (3H, s), 2.78 (2H, br d, J=11.53 Hz), 3.82-3.94 (1H, m), 7.23(1H, dd, J=7.96, 4.67 Hz), 7.52 (1H, d, J=4.39 Hz), 8.09-8.13 (2H, m),8.21 (1H, dd, J=8.78, 1.92 Hz), 8.30-8.35 (2H, m), 8.43 (1H, d, J=1.92Hz), 8.78 (1H, d, J=7.68 Hz), 8.89 (1H, d, J=4.39 Hz), 12.12 (1H, s);ESIMS found for C₂₃H₂₃N₅O m/z 386.1 (M+1).

6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)quinoxaline 90

Orange solid (25 mg, 0.102 mmol, 28.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 7.25 (1H, dd, J=7.96, 4.67 Hz), 8.13 (1H, d, J=8.78 Hz), 8.25 (1H,d, J=2.74 Hz), 8.33 (1H, br dd, J=13.04, 1.78 Hz), 8.33 (1H, d, J=1.92Hz), 8.37 (1H, d, J=1.92 Hz), 8.48 (1H, dd, J=7.96, 0.82 Hz), 8.87 (1H,d, J=1.65 Hz), 8.94 (1H, d, J=1.92 Hz), 12.19 (1H, br s); ESIMS foundfor C₁₅H₁₀N₄ m/z 247.1 (M+1).

2-((1-Methylpiperidin-4-yl)oxy)-7-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline 91

Pinkish solid (39.6 mg, 0.110 mmol, 35.5% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.75-1.85 (2H, m), 2.09 (2H, br dd, J=8.78, 3.84 Hz),2.21 (3H, s), 2.23-2.29 (2H, m), 2.63-2.72 (2H, m), 5.22-5.32 (1H, m),7.23 (1H, dd, J=7.96, 4.67 Hz), 8.00-8.03 (1H, m), 8.05-8.08 (2H, m),8.19 (1H, d, J=1.37 Hz), 8.32 (1H, dd, J=4.67, 1.65 Hz), 8.43 (1H, dd,J=7.96, 1.37 Hz), 8.47 (1H, s), 12.14 (1H, br s); ESIMS found forC₂₁H₂₁N₅O m/z 360.1 (M+1).

N-(1-Methylpiperidin-4-yl)-7-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxalin-2-amine 92

Brown solid (4.0 mg, 0.011 mmol, 2.7% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.45-1.61 (2H, m), 1.81-1.88 (2H, m), 2.03-2.11 (2H, m), 2.19 (3H,s), 2.76 (2H, br d, J=11.80 Hz), 3.86-3.97 (1H, m), 7.19-7.22 (1H, m),7.49 (1H, br d, J=7.41 Hz), 8.07 (1H, s), 8.09-8.11 (1H, m), 8.21 (1H,s), 8.29-8.32 (2H, m), 8.37 (1H, dd, J=7.96, 1.37 Hz), 8.39 (1H, dd,J=8.10, 1.51 Hz), 12.03 (1H, br s); ESIMS found for C₂₁H₂₂N₆ m/z 359.1(M+1).

6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)quinazoline 93

Dark yellow solid (20 mg, 0.081 mmol, 38.3% yield). ¹H NMR (500 MHz,DMSO-d₆) δ ppm 7.25 (1H, dd, J=7.96, 4.67 Hz), 8.05 (1H, d, J=8.78 Hz),8.20 (1H, d, J=1.92 Hz), 8.34 (1H, dd, J=4.67, 1.65 Hz), 8.47 (1H, dd,J=8.92, 2.06 Hz), 8.51 (1H, d, J=1.92 Hz), 8.59 (1H, dd, J=7.96, 1.65Hz), 9.24 (1H, s), 9.67 (1H, s), 12.15 (1H, br s); ESIMS found forC₁₅H₁₀N₄ m/z 247.05 (M+1).

4-(4-Methylpiperazin-1-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl) quinazoline95

Yellow solid (37.0 mg, 0.107 mmol, 33.2% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.26 (3H, s), 2.53-2.58 (4H, m), 3.76-3.84 (4H, m), 7.24(1H, dd, J=7.68, 4.67 Hz), 7.87 (1H, d, J=8.51 Hz), 8.08 (1H, d, J=2.19Hz), 8.14 (1H, d, J=1.92 Hz), 8.21 (1H, dd, J=8.78, 1.92 Hz), 8.31 (1H,br d, J=11.53 Hz), 8.32 (1H, d, J=1.10 Hz), 8.61 (1H, s), 12.09 (1H, brs); ESIMS found for C₂₀H₂₀N₆ m/z 345.2 (M+1).

6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-4-(4,7-diazaspiro[2.5]octan-7-yl)quinazoline 96

White solid (17 mg, 0.048 mmol, 55.8% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 0.44-0.55 (4H, m), 3.00 (2H, br d, J=3.84 Hz), 3.66 (2H, s),3.75-3.83 (2H, m), 7.23 (1H, dd, J=7.96, 4.67 Hz), 7.85 (1H, d, J=8.51Hz), 8.04 (1H, s), 8.10 (1H, d, J=1.92 Hz), 8.18 (1H, dd, J=8.78, 1.92Hz), 8.27 (1H, dd, J=7.96, 1.65 Hz), 8.32 (1H, dd, J=4.67, 1.37 Hz),8.58 (1H, s), 12.07 (1H, br s); ESIMS found for C₂₁H₂₀N₆ m/z 357.1(M+1).

6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-4-(5,8-diazaspiro[3.5]nonan-8-yl)quinazoline 97

Beige solid (25 mg, 0.068 mmol, 12.5% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.60-1.69 (1H, m), 1.70-1.76 (1H, m), 1.79-1.90 (2H, m), 1.94-2.03(2H, m), 2.90-2.97 (2H, m), 3.70 (4H, s), 7.22 (1H, dd, J=7.96, 4.67Hz), 7.87 (1H, d, J=8.51 Hz), 8.04 (1H, d, J=2.47 Hz), 8.16 (1H, d,J=1.65 Hz), 8.20 (1H, dd, J=8.64, 1.78 Hz), 8.29 (1H, d, J=7.96 Hz),8.32 (1H, dd, J=4.53, 1.24 Hz), 8.60 (1H, s), 12.09 (1H, br s); ESIMSfound for C₂₂H₂₂N₆ m/z 371.1 (M+1).

9-(6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-yl)-6,9-diazaspiro[4.5]decane 98

Beige solid (75 mg, 0.195 mmol, 33.9% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.43-1.50 (2H, m), 1.51-1.57 (2H, m), 1.57-1.66 (4H, m), 2.94-3.03(2H, m), 3.58 (2H, s), 3.65-3.73 (2H, m), 7.22 (1H, dd, J=7.96, 4.67Hz), 7.86 (1H, d, J=8.51 Hz), 8.03 (1H, d, J=1.92 Hz), 8.15 (1H, d,J=1.37 Hz), 8.18 (1H, dd, J=8.78, 1.92 Hz), 8.28 (1H, dd, J=7.96, 1.37Hz), 8.32 (1H, dd, J=4.53, 1.24 Hz), 8.58 (1H, s), 12.08 (1H, br s);ESIMS found for C₂₃H₂₄N₆ m/z 385.1 (M+1).

4-((1-Methylpiperidin-4-yl)oxy)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline 99

Off-white solid (30.7 mg, 0.085 mmol, 27.5% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.86-1.97 (2H, m), 2.02-2.12 (2H, m), 2.23 (3H, s),2.29-2.40 (2H, m), 2.64 (2H, br dd, J=4.67, 2.47 Hz), 5.38-5.47 (1H, m),7.24 (1H, dd, J=7.96, 4.67 Hz), 7.95 (1H, d, J=8.78 Hz), 8.15 (1H, d,J=2.47 Hz), 8.32-8.35 (2H, m), 8.35-8.37 (1H, m), 8.38 (1H, d, J=1.92Hz), 8.74 (1H, s), 12.15 (1H, br s); ESIMS found for C₂₁H₂₁N₅O m/z 360.1(M+1).

N-(1-Methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine 100

Grey solid (40.0 mg, 0.112 mmol, 27.2% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.70 (2H, qd, J=12.03, 3.70 Hz), 1.89-2.04 (4H, m), 2.20 (3H, s),2.84 (2H, br d, J=11.53 Hz), 4.13-4.25 (1H, m), 7.22 (1H, dd, J=7.96,4.67 Hz), 7.73 (1H, d, J=8.51 Hz), 7.95 (1H, d, J=7.68 Hz), 8.00 (1H, d,J=1.10 Hz), 8.14 (1H, dd, J=8.51, 1.92 Hz), 8.31 (1H, dd, J=4.53, 1.24Hz), 8.40 (1H, dd, J=7.96, 1.10 Hz), 8.43 (1H, s), 8.53 (1H, d, J=1.65Hz), 12.04 (1H, br s); ESIMS found for C₂₁H₂₂N₆ m/z 359.1 (M+1).

N-(6-Methoxypyridin-3-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine 101

White solid (11 mg, 0.030 mmol, 25.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.88 (3H, s), 6.91 (1H, d, J=8.78 Hz), 7.23 (1H, dd, J=7.96, 4.67Hz), 7.84 (1H, d, J=8.51 Hz), 8.05-8.10 (2H, m), 8.26 (1H, dd, J=8.64,1.78 Hz), 8.33 (1H, dd, J=4.67, 1.37 Hz), 8.48-8.50 (2H, m), 8.52 (1H,dd, J=8.23, 1.37 Hz), 8.71 (1H, d, J=1.65 Hz), 9.89 (1H, s), 12.08 (1H,br s); ESIMS found for C₂₁H₁₆N₆O m/z 369.0 (M+1).

N-(6-((1-Methylpiperidin-4-yl)oxy)pyridin-3-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine 102

White solid (48 mg, 0.106 mmol, 44.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.69 (2H, dtd, J=12.66, 9.25, 9.25, 3.70 Hz), 1.95-2.03 (2H, m),2.13-2.20 (2H, m), 2.19 (3H, s), 2.58-2.70 (2H, m), 4.98 (1H, tt,J=8.68, 4.22 Hz), 6.86 (1H, d, J=8.78 Hz), 7.23 (1H, dd, J=7.96, 4.67Hz), 7.84 (1H, d, J=8.78 Hz), 8.03-8.08 (2H, m), 8.26 (1H, dd, J=8.65,1.78 Hz), 8.33 (1H, dd, J=4.67, 1.37 Hz), 8.46 (1H, d, J=2.74 Hz), 8.49(1H, s), 8.52 (1H, dd, J=7.96, 1.10 Hz), 8.70 (1H, d, J=1.65 Hz), 9.87(1H, s), 12.08 (1H, br s); ESIMS found for C₂₆H₂₅N₇O m/z 452.1 (M+1).

N-(Pyridin-3-ylmethyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine103

Off-white solid (32 mg, 0.091 mmol, 28.6% yield). ¹H NMR (500 MHz,DMSO-d₆) δ ppm 4.85 (2H, br d, J=5.49 Hz), 7.22 (1H, br dd, J=7.82, 4.53Hz), 7.35 (1H, br dd, J=7.68, 4.94 Hz), 7.76 (1H, br d, J=8.51 Hz), 7.80(1H, br d, J=7.68 Hz), 8.01 (1H, br d, J=1.92 Hz), 8.19 (1H, br d,J=7.96 Hz), 8.31 (1H, br d, J=4.12 Hz), 8.44 (1H, s), 8.46 (1H, br d,J=4.12 Hz), 8.49 (1H, br d, J=7.68 Hz), 8.52 (1H, s), 8.65 (1H, br s),8.93 (1H, br t, J=4.80 Hz), 12.04 (1H, br s); ESIMS found for C₂₁H₁₆N₆m/z 353.0 (M+1).

N-((6-(4-Methylpiperazin-1-yl)pyridin-3-yl)methyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine104

Lime green solid (20 mg, 0.044 mmol, 22.9% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.18 (3H, s), 2.33-2.38 (4H, m), 3.39-3.46 (4H, m), 4.68(2H, d, J=5.76 Hz), 6.79 (1H, d, J=8.78 Hz), 7.22 (1H, dd, J=7.96, 4.67Hz), 7.59 (1H, dd, J=8.78, 2.47 Hz), 7.74 (1H, d, J=8.78 Hz), 7.99 (1H,s), 8.16 (1H, dd, J=8.78, 1.92 Hz), 8.19 (1H, d, J=2.47 Hz), 8.31 (1H,dd, J=4.53, 1.51 Hz), 8.45 (1H, s), 8.46 (1H, dd, J=7.96, 1.37 Hz), 8.48(1H, d, J=1.65 Hz), 8.77 (1H, t, J=5.76 Hz), 12.03 (1H, br s); ESIMSfound for C₂₆H₂₆N₈ m/z 451.1 (M+1).

N-((2-(4-Methylpiperazin-1-yl)pyridin-4-yl)methyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine 105

White solid (21 mg, 0.047 mmol, 24.1% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 2.19 (3H, s), 2.36 (4H, t, J=4.94 Hz), 3.40-3.48 (4H, m), 4.75(2H, d, J=5.76 Hz), 6.64 (1H, d, J=4.94 Hz), 6.83 (1H, s), 7.22 (1H, dd,J=7.96, 4.67 Hz), 7.76 (1H, d, J=8.51 Hz), 8.01 (1H, d, J=3.02 Hz), 8.02(1H, s), 8.19 (1H, dd, J=8.65, 1.78 Hz), 8.32 (1H, dd, J=4.53, 1.51 Hz),8.41 (1H, s), 8.50 (1H, dd, J=8.10, 1.24 Hz), 8.54 (1H, d, J=1.65 Hz),8.87 (1H, t, J=5.90 Hz), 12.04 (1H, br s); ESIMS found for C₂₆H₂₆N₈ m/z451.1 (M+1).

N-(1-Methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline-4-carboxamide 106

Yellow solid (26 mg, 0.067 mmol, 29.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.61-1.76 (2H, m), 1.81-1.90 (2H, m), 1.98-2.09 (2H, m), 2.15-2.22(3H, m), 2.78 (2H, br d, J=11.80 Hz), 3.84-3.98 (1H, m), 7.29 (1H, dd,J=7.96, 4.67 Hz), 8.12 (1H, d, J=8.78 Hz), 8.23 (1H, s), 8.35 (1H, dd,J=4.67, 1.37 Hz), 8.39 (1H, dd, J=7.96, 1.37 Hz), 8.51 (1H, dd, J=8.92,2.06 Hz), 9.01 (1H, d, J=7.96 Hz), 9.11 (1H, d, J=1.92 Hz), 9.31 (1H,s), 12.22 (1H, br s); ESIMS found for C₂₂H₂₂N₆O m/z 387.1 (M+1).

(5-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-morpholinopiperidin-1-yl)methanone107

Light brown solid (60 mg, 0.139 mmol, 33.6% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.43 (2H, qd, J=11.96, 3.83 Hz), 1.86 (2H, br d, J=11.50Hz), 2.41-2.46 (1H, m), 2.46-2.49 (4H, m), 2.96-3.09 (2H, m), 3.52-3.61(4H, m), 4.34 (2H, br d, J=12.59 Hz), 7.27 (1H, dd, J=7.80, 4.79 Hz),7.48 (1H, dd, J=7.12, 1.92 Hz), 8.16 (1H, d, J=1.37 Hz), 8.21-8.24 (2H,m), 8.31-8.35 (2H, m), 8.77 (1H, d, J=7.39 Hz), 12.22 (1H, br s); ESIMSfound for C₂₄H₂₆N₆O₂ m/z 431.2 (M+1).

(6-(1H-Pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-yl)(4,7-diazaspiro[2.5]octan-7-yl)methanone 108

Beige solid (5 mg, 0.013 mmol, 48.5% yield). ¹H NMR (500 MHz, DMSO-d₆) δppm 0.12-0.25 (1H, m), 0.26-0.37 (1H, m), 0.49-0.57 (1H, m),0.65-0.74(1H, m), 2.61 (1H, br d, J=4.67 Hz), 2.89-2.99 (1H, m), 3.09(1H, s), 3.19 (1H, br d, J=3.02 Hz), 3.68 (1H, s), 3.77-3.86 (1H, m),7.27 (1H, td, J=7.55, 4.67 Hz), 8.09-8.14 (1H, m), 8.14-8.19 (1H, m),8.22 (1H, d, J=6.04 Hz), 8.30 (1H, td, J=7.89, 1.23 Hz), 8.36 (1H, dd,J=4.25, 2.33 Hz), 8.47-8.57 (1H, m), 9.21-9.30 (1H, m), 12.25 (1H, brs); ESIMS found for C₂₂H₂₀N₆O m/z 385.1 (M+1).

5-(4-Methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide128

Off-white solid (16 mg, 0.040 mmol, 14.7% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.57 (2H, qd, J=11.96, 3.83 Hz), 1.80 (2H, br dd,J=12.05, 1.92 Hz), 1.96 (2H, br t, J=10.81 Hz), 2.17 (3H, s), 2.78 (2H,br d, J=11.77 Hz), 3.70-3.82 (1H, m), 3.99 (3H, s), 6.77 (1H, d, J=5.75Hz), 7.36 (1H, dd, J=7.39, 2.19 Hz), 7.82 (1H, d, J=2.74 Hz), 7.86 (1H,d, J=7.94 Hz), 8.19 (1H, d, J=5.48 Hz), 8.52 (1H, s), 8.65 (1H, dd,J=7.12, 0.82 Hz), 8.70 (1H, d, J=1.37 Hz), 12.06 (1H, br s); ESIMS foundfor C₂₂H₂₄N₆O₂ m/z 405.2 (M+1).

(5-(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone215

Light grey solid (12 mg, 0.030 mmol, 13.2% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.22 (3H, s), 2.39 (4H, t, J=5.08 Hz), 3.64-3.71 (4H, m),7.48 (1H, dd, J=7.27, 2.06 Hz), 8.10 (1H, d, J=1.37 Hz), 8.25 (1H, s),8.32 (1H, s), 8.35 (2H, q, J=2.47 Hz), 8.75-8.82 (1H, m), 12.48 (1H, brs); ESIMS found for C₂₀H₁₉ClN₆O m/z 395.0 (M+1).

7-(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one226

White solid (28 mg, 0.076 mmol, 59.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.55-1.66 (2H, m), 1.84 (2H, br d, J=13.45 Hz), 2.69 (2H, dt,J=12.62, 3.98 Hz), 2.78 (2H, s), 2.85-2.94 (2H, m), 7.37 (1H, d, J=1.37Hz), 7.45 (1H, dd, J=7.96, 1.65 Hz), 7.76 (1H, d, J=8.23 Hz), 8.23 (1H,s), 8.30 (1H, d, J=2.47 Hz), 8.39 (1H, d, J=2.20 Hz), 12.40 (1H, br s);ESIMS found for C₂₀H₁₈ClN₃O₂ m/z 368.1 (M+1).

(5-(5-Fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone257

Light yellow solid (20.0 mg, 0.053 mmol, 38.8% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.21 (3H, s), 2.38 (4H, t, J=4.94 Hz), 3.64-3.70 (4H, m),7.51 (1H, dd, J=7.27, 2.06 Hz), 8.14 (1H, d, J=1.37 Hz), 8.26 (1H, s),8.44 (1H, s), 8.61 (1H, d, J=1.65 Hz), 8.70 (1H, d, J=1.65 Hz), 8.82(1H, d, J=7.41 Hz), 12.75 (1H, br s); ESIMS found for C₂₀H_(19N)FN₆O m/z379.1 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole325

Yellow solid (15 mg, 0.037 mmol, 26.9% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.62 (6H, d, J=6.86 Hz), 2.29 (3H, s), 2.58-2.61 (4H, m), 2.59(3H, s), 3.04 (2H, br d, J=2.74 Hz), 4.81 (1H, spt, J=6.90 Hz), 6.20(1H, t, J=3.43 Hz), 7.29 (1H, dd, J=11.94, 0.96 Hz), 7.67 (1H, d, J=1.10Hz), 7.91 (1H, d, J=2.47 Hz), 8.15 (1H, d, J=1.92 Hz), 8.43 (1H, d,J=1.92 Hz), 11.91 (1H, s); ESIMS found for C₂₄H₂₆FN₅ m/z 404.2 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole367

Off-white solid (5 mg, 0.012 mmol, 22.4% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.61 (6H, d, J=6.86 Hz), 2.24 (3H, s), 2.51-2.53 (4H, m),2.59 (3H, s), 3.11-3.16 (4H, m), 4.80 (1H, spt, J=6.80 Hz), 7.22-7.28(1H, m), 7.63 (1H, d, J=0.82 Hz), 7.67 (1H, d, J=2.74 Hz), 7.82 (1H, s),8.15 (1H, d, J=2.47 Hz), 11.67 (1H, br s); ESIMS found for C₂₃H₂₇FN₆ m/z407.25 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole409

White solid (13 mg, 0.031 mmol, 35.5% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.63 (6H, d, J=7.14 Hz), 2.14 (3H, s), 2.20-2.35 (4H, m),2.36-2.49 (4H, m), 2.59 (3H, s), 3.62 (2H, s), 4.81 (1H, spt, J=6.86Hz), 7.28 (1H, dd, J=12.08, 1.10 Hz), 7.66 (1H, d, J=1.10 Hz), 7.93 (1H,d, J=2.47 Hz), 8.16 (1H, d, J=1.65 Hz), 8.19 (1H, d, J=1.65 Hz), 11.88(1H, s); ESIMS found for C₂₄H₂₉FN₆ m/z 421.1 (M+1).

6-(5-((4-Methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline 439

Beige solid (6 mg, 0.017 mmol, 28.6% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 2.13 (3H, s), 2.19-2.36 (4H, m), 2.36-2.49 (4H, m), 3.64 (2H, s),8.14 (1H, d, J=8.78 Hz), 8.23 (1H, s), 8.25 (1H, d, J=1.65 Hz), 8.31(1H, dd, J=8.78, 1.92 Hz), 8.35 (2H, dd, J=3.29, 1.92 Hz), 8.88 (1H, d,J=1.92 Hz), 8.94 (1H, d, J=1.92 Hz), 12.16 (1H, s); ESIMS found forC₂₁H₂₂N₆ m/z 359.1 (M+1).

3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide451

White solid (5 mg, 0.011 mmol, 25.2% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.54-1.67 (2H, m), 1.63 (6H, d, J=6.86 Hz), 1.77-1.83 (2H, m),1.92-1.99 (2H, m), 2.17 (3H, s), 2.60 (3H, s), 2.77 (2H, br d, J=11.53Hz), 3.72-3.84 (1H, m), 4.82(1H, spt, J=6.86 Hz), 7.33 (1H, dd, J=11.94,0.96 Hz), 7.72 (1H, d, J=1.10 Hz), 8.01 (1H, s), 8.38 (1H, d, J=7.68Hz), 8.67 (1H, d, J=1.92 Hz), 8.76 (1H, d, J=1.92 Hz), 12.19 (1H, br s);ESIMS found for C₂₅H₂₉FN₆O m/z 449.2 (M+1).

N-(1-Methylpiperidin-4-yl)-3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide 482

Yellowish white solid (4 mg, 0.010 mmol, 40.0% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.58-1.68 (2H, m), 1.80-1.87 (2H, m), 1.93-2.01 (2H, m),2.17 (3H, s), 2.79 (2H, br d, J=11.80 Hz), 3.75-3.84 (1H, m), 8.10 (1H,d, J=8.78 Hz), 8.24 (1H, s), 8.40 (1H, d, J=7.68 Hz), 8.48 (1H, dd,J=8.64, 2.06 Hz), 8.51 (1H, d, J=1.65 Hz), 8.81 (1H, d, J=1.92 Hz), 8.87(1H, d, J=2.20 Hz), 9.27 (1H, s), 9.68 (1H, s), 12.42 (1H, br s); ESIMSfound for C₂₂H₂₂N₆O m/z 387.1 (M+1).

(3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone493

Pale yellow solid (3 mg, 0.007 mmol, 4.9% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.62 (6H, d, J=6.86 Hz), 2.20 (3H, s), 2.35 (4H, br s),2.60 (3H, s), 3.48-3.65 (4H, m), 4.82 (1H, spt, J=6.93 Hz), 7.30 (1H,dd, J=11.94, 0.96 Hz), 7.68 (1H, d, J=1.10 Hz), 8.04 (1H, s), 8.24 (1H,d, J=1.92 Hz), 8.34 (1H, d, J=1.92 Hz), 12.19 (1H, s); ESIMS found forC₂₄H₂₇FN₆O m/z 435.2 (M+1).

(3-(3-(1-Methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone502

Light orange solid (10 mg, 0.023 mmol, 22.5% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.18 (3H, s), 2.27-2.39 (4H, m), 3.49-3.67 (4H, m), 3.91(3H, s), 7.30 (1H, dd, J=7.14, 1.92 Hz), 7.90 (1H, s), 8.00 (1H, d,J=1.10 Hz), 8.18-8.21 (2H, m), 8.28 (1H, d, J=2.47 Hz), 8.35 (1H, d,J=1.65 Hz), 8.36-8.38 (1H, m), 8.67-8.72 (1H, m), 12.38 (1H, br s);ESIMS found for C₂₄H₂₄N₈O m/z 441.1 (M+1).

8-(5-(4-Methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one521

Light grey solid (6 mg, 0.015 mmol, 25.9% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.20 (3H, s), 2.27-2.42 (4H, m), 3.37 (2H, q, J=4.94 Hz),3.42-3.71 (4H, m), 4.31-4.38 (2H, m), 7.35 (1H, d, J=1.65 Hz), 7.52 (1H,dd, J=8.23, 1.65 Hz), 7.87 (1H, d, J=8.23 Hz), 8.13 (1H, s), 8.28 (1H,br t, J=5.21 Hz), 8.30-8.32 (1H, m), 8.33 (1H, d, J=1.92 Hz), 12.31 (1H,br s); ESIMS found for C₂₂H₂₃N₅O₃ m/z 406.1 (M+1).

(3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone535

Off-white solid (18.0 mg, 0.039 mmol, 27.5% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.61 (6H, d, J=6.86 Hz), 1.77-1.86 (4H, m), 2.18 (3H, s),2.19-2.29 (2H, m), 2.63-2.75 (2H, m), 4.08-4.25 (1H, m), 4.54-4.69 (1H,m), 4.82 (1H, spt, J=6.93 Hz), 7.30 (1H, dd, J=11.94, 0.96 Hz), 7.69(1H, d, J=1.37 Hz), 8.04 (1H, d, J=2.47 Hz), 8.30 (1H, d, J=1.92 Hz),8.42 (1H, d, J=1.92 Hz), 12.22 (1H, br s); ESIMS found for C₂₆H₂₉FN₆Om/z 461.2 (M+1).

7-(5-(2-Methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one573

Beige solid (3 mg, 0.007 mmol, 22.8% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 2.05 (3H, br s), 3.24 (2H, br s), 3.52 (2H, br d, J=7.14 Hz), 3.99(2H, br d, J=4.67 Hz), 4.09-4.15 (2H, m), 4.73 (2H, br s), 6.81 (1H, s),7.03 (1H, d, J=1.10 Hz), 7.52 (1H, s), 7.66 (1H, br s), 7.82 (1H, s),8.32 (1H, s), 8.35 (1H, s), 11.93 (1H, br s); ESIMS found for C₂₂H₂₁N₇O₂m/z 416.1 (M+1).

(3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone577

Beige solid (10 mg, 0.021 mmol, 14.9% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.60 (6H, d, J=6.86 Hz), 2.05 (3H, s), 2.59 (3H, s), 3.95 (2H, brs), 4.00 (2H, br d, J=4.67 Hz), 4.73 (2H, s), 4.81 (1H, dt, J=13.79,6.96 Hz), 6.80 (1H, s), 7.31 (1H, d, J=12.08 Hz), 7.68 (1H, s), 8.07(1H, s), 8.36 (1H, d, J=1.37 Hz), 8.42 (1H, d, J=1.65 Hz), 12.17 (1H, brs); ESIMS found for C₂₆H₂₆FN₇O m/z 472.1 (M+1).

N-(3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide619

Yellow solid (30 mg, 0.067 mmol, 60.6% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.62 (6H, d, J=6.86 Hz), 1.65-1.74 (2H, m), 1.75-1.83 (2H, m),1.88 (2H, td, J=11.60, 2.06 Hz), 2.16 (3H, s), 2.31 (1H, tt, J=11.46,3.91 Hz), 2.59 (3H, s), 2.82 (2H, br d, J=11.53 Hz), 4.79 (1H, spt,J=6.93 Hz), 7.24 (1H, dd, J=12.08, 0.82 Hz), 7.65 (1H, d, J=1.10 Hz),7.92 (1H, s), 8.40 (1H, d, J=2.20 Hz), 8.66 (1H, d, J=2.20 Hz), 9.95(1H, s), 11.84 (1H, s); ESIMS found for C₂₅H₂₉FN₆O m/z 449.2 (M+1).

1-Methyl-N-(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide 648

Yellow solid (5 mg, 0.013 mmol, 15.2% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.65-1.77 (2H, m), 1.79-1.85 (2H, m), 1.97 (2H, br t, J=11.11 Hz),2.22 (3H, s), 2.29-2.39 (1H, m), 2.89 (2H, br d, J=11.53 Hz), 7.54 (1H,dd, J=8.37, 4.25 Hz), 8.04 (1H, d, J=2.74 Hz), 8.06-8.10 (1H, m),8.11-8.14 (1H, m), 8.19 (1H, s), 8.38 (1H, dd, J=8.37, 1.24 Hz), 8.48(1H, d, J=2.20 Hz), 8.71 (1H, d, J=2.20 Hz), 8.85 (1H, dd, J=4.12, 1.65Hz), 9.99 (1H, s), 11.99 (1H, s); ESIMS found for C₂₃H₂₃N₅O m/z 386.15(M+1).

3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide661

Beige solid (48 mg, 0.096 mmol, 96.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.63 (6H, d, J=7.14 Hz), 1.80-1.90 (2H, m), 2.01 (2H, br d,J=10.15 Hz), 2.61 (3H, s), 2.68-2.79 (2H, m), 3.15 (2H, br d, J=12.90Hz), 4.28 (1H, tt, J=11.39, 4.25 Hz), 4.77-4.90 (1H, m), 7.37(1H, d,J=11.53 Hz), 7.61 (1H, s), 7.73 (1H, d, J=0.82 Hz), 8.06 (1H, s), 8.08(1H, s), 8.79 (1H, d, J=2.20 Hz), 8.87 (1H, d, J=1.92 Hz), 10.55 (1H,s), 12.26 (1H, br s); ESIMS found for C₂₇H₂₉FN₈O m/z 501.2 (M+1).

3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide703

Off-white solid (5 mg, 0.010 mmol, 10.8% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.63 (6H, d, J=6.86 Hz), 1.91-1.98 (4H, m), 2.01-2.08(2H, m), 2.20 (3H, s), 2.61 (3H, s), 2.85 (2H, br d, J=11.25 Hz), 4.11(1H, tt, J=10.33, 5.32 Hz), 4.83 (1H, quin, J=6.93 Hz), 7.37 (1H, d,J=12.08 Hz), 7.62 (1H, s), 7.73 (1H, d, J=0.82 Hz), 8.06 (1H, s), 8.07(1H, s), 8.79 (1H, d, J=2.20 Hz), 8.87 (1H, d, J=1.92 Hz), 10.54 (1H,s), 12.27 (1H, br s); ESIMS found for C₂₈H₃₁FN₈O m/z 515.3 (M+1).

3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide787

Brown solid (25 mg, 0.048 mmol, 12.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.63 (6H, d, J=7.14 Hz), 2.23 (3H, s), 2.43 (4H, br s), 2.60 (3H,s), 3.45 (4H, br s), 4.82 (1H, spt, J=7.00 Hz), 6.87 (1H, d, J=9.06 Hz),7.38 (1H, dd, J=11.94, 0.96 Hz), 7.75 (1H, d, J=1.10 Hz), 7.93 (1H, dd,J=9.19, 2.61 Hz), 8.06 (1H, d, J=2.74 Hz), 8.46 (1H, d, J=2.47 Hz), 8.81(1H, d, J=1.92 Hz), 8.88 (1H, d, J=1.92 Hz), 10.27 (1H, s), 12.27 (1H,s); ESIMS found for C₂₉H₃₁FN₈O m/z 527.3 (M+1).

3-([1,2,4]Triazolo[1,5-a]pyridin-7-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide 792

Beige solid (5 mg, 0.011 mmol, 14.9% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 2.19-2.26 (3H, m), 2.37-2.44 (4H, m), 3.42-3.50 (4H, m), 6.89 (1H,d, J=9.03 Hz), 7.70 (1H, dd, J=7.26, 1.78 Hz), 7.92 (1H, dd, J=9.17,2.60 Hz), 8.28 (1H, d, J=1.09 Hz), 8.41 (1H, s), 8.47 (1H, d, J=2.74Hz), 8.49 (1H, s), 8.92 (1H, d, J=1.92 Hz), 8.98-9.01 (1H, m), 9.02 (1H,d, J=1.92 Hz), 10.36 (1H, s), 12.58 (1H, br s); ESIMS found forC₂₄H₂₃N₉O m/z 454.1 (M+1).

N-(6-(4-Methylpiperazin-1-yl)pyridin-3-yl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide802

Beige solid (6 mg, 0.011 mmol, 17.8% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.51-1.65 (6H, m), 2.22 (3H, s), 2.38-2.46 (4H, m), 3.41-3.49 (4H,m), 3.60-3.69 (4H, m), 6.88 (1H, d, J=9.06 Hz), 7.52 (1H, dd, J=7.41,1.92 Hz), 7.93 (1H, dd, J=9.06, 2.74 Hz), 8.15 (1H, d, J=1.37 Hz), 8.21(1H, s), 8.33 (1H, s), 8.48 (1H, d, J=2.74 Hz), 8.81-8.85 (1H, m), 8.88(1H, d, J=1.92 Hz), 8.92 (1H, d, J=1.92 Hz), 10.31 (1H, s), 12.53 (1H,br s); ESIMS found for C₃₁H₃₃N₉O₂ m/z 564.2 (M+1).

3-(4,4-Dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide813

Beige solid (5 mg, 0.010 mmol, 13.6% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.37 (6H, s), 2.22 (3H, s), 2.37-2.45 (4H, m), 3.21 (2H, d, J=2.74Hz), 3.41-3.50 (4H, m), 6.87 (1H, d, J=9.31 Hz), 7.74 (1H, d, J=1.37Hz), 7.78 (1H, dd, J=8.08, 1.78 Hz), 7.91-7.94 (2H, m), 7.96 (1H, d,J=8.21 Hz), 8.16 (1H, s), 8.47 (1H, d, J=2.74 Hz), 8.83 (1H, d, J=2.19Hz), 8.88 (1H, d, J=1.92 Hz), 10.27 (1H, s), 12.39 (1H, br s); ESIMSfound for C₂₉H₃₁N₇O₂ m/z 510.2 (M+1).

N-(6-(4-Methylpiperazin-1-yl)pyridin-3-yl)-3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide817

Beige solid (32 mg, 0.069 mmol, 40.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 2.22 (3H, s), 2.41 (4H, t, J=4.94 Hz), 3.42-3.50 (4H, m), 6.89(1H, d, J=9.06 Hz), 7.92 (1H, dd, J=9.06, 2.74 Hz), 8.18 (1H, d, J=8.78Hz), 8.35-8.40 (2H, m), 8.49 (1H, d, J=2.47 Hz), 8.50 (1H, d, J=1.92Hz), 8.90 (1H, d, J=1.92 Hz), 8.93 (1H, d, J=1.92 Hz), 8.96 (1H, d,J=1.65 Hz), 9.02 (1H, d, J=1.65 Hz), 10.35 (1H, s), 12.53 (1H, br s);ESIMS found for C₂₆H₂₄N₈O m/z 465.1 (M+1).

N-(3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide829

Off-white solid (12 mg, 0.023 mmol, 71.7% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.63 (6H, d, J=6.86 Hz), 2.59 (3H, s), 2.80-2.87 (4H, m),3.50-3.56 (4H, m), 4.80 (1H, spt, J=6.86 Hz), 7.10 (1H, d, J=5.21 Hz),7.26-7.30 (2H, m), 7.69(1H, d, J=1.10 Hz), 7.98 (1H, d, J=2.47 Hz), 8.27(1H, d, J=4.94 Hz), 8.58 (1H, d, J=2.20 Hz), 8.75 (1H, d, J=2.20 Hz),10.45 (1H, s), 11.94 (1H, s); ESIMS found for C₂₈H₂₉FN₈O m/z 513.3(M+1).

3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine871

Off-white solid (5 mg, 0.010 mmol, 10.7% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.58 (6H, d, J=6.86 Hz), 2.18 (3H, s), 2.31-2.38 (4H, m),2.58 (3H, s), 3.33-3.37 (4H, m), 4.79 (1H, spt, J=6.93 Hz), 6.17 (1H, d,J=1.65 Hz), 6.27 (1H, dd, J=5.76, 1.92 Hz), 7.25 (1H, dd, J=12.08, 1.10Hz), 7.63 (1H, d, J=1.10 Hz), 7.78 (1H, d, J=5.49 Hz), 7.95 (1H, s),8.01 (1H, d, J=2.47 Hz), 8.15 (1H, d, J=2.47 Hz), 8.43 (1H, s), 11.92(1H, br s); ESIMS found for C₂₈H₃₁FN₈ m/z 499.3 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole913

White solid (22 mg, 0.057 mmol, 43.5% yield ¹H NMR (499 MHz, DMSO-d₆) δppm 1.62 (6H, d, J=6.86 Hz), 2.60 (3H, s), 4.82 (1H, spt, J=6.95 Hz),7.35-7.40 (2H, m), 7.50 (2H, t, J=7.68 Hz), 7.74 (1H, d, J=1.37 Hz),7.76 (1H, d, J=1.10 Hz), 7.77-7.78 (1H, m), 7.99 (1H, d, J=1.37 Hz),8.40 (1H, d, J=1.92 Hz), 8.58 (1H, d, J=1.92 Hz), 12.03 (1H, br s);ESIMS found for C₂₄H₂₁FN₄ m/z 385.2 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole 955

White solid (47 mg, 0.118 mmol, 63.5% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.59 (6H, d, J=7.14 Hz), 2.31 (3H, s), 2.58 (3H, s), 4.79 (1H,spt, J=6.82 Hz), 7.28-7.33 (3H, m), 7.33-7.37 (2H, m), 7.68 (1H, d,J=1.10 Hz), 8.00 (1H, d, J=2.74 Hz), 8.14 (1H, d, J=1.92 Hz), 8.26 (1H,d, J=1.92 Hz), 12.03 (1H, br s); ESIMS found for C₂₅H₂₃FN₄ m/z 399.2(M+1).

6-(5-(3,4-Difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole 997

White solid (29 mg, 0.058 mmol, 69.5% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.63 (6H, d, J=6.86 Hz), 2.60 (3H, s), 2.85-2.91 (4H, m),3.03-3.10 (4H, m), 4.83 (1H, spt, J=6.86 Hz), 7.15 (1H, br d, J=7.14Hz), 7.36 (1H, dd, J=12.08, 0.82 Hz), 7.42 (1H, ddd, J=11.25, 6.59, 1.92Hz), 7.78 (1H, d, J=1.10 Hz), 7.99 (1H, d, J=2.47 Hz), 8.40 (1H, d,J=2.20 Hz), 8.59 (1H, d, J=2.20 Hz), 12.06 (1H, br s); ESIMS found forC₂₈H₂₇F₃N₆ m/z 505.3 (M+1).

6-(5-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine 1036

Tan solid (4 mg, 0.013 mmol, 19.9% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 3.90 (3H, s), 7.58 (1H, d, J=0.82 Hz), 7.61-7.65 (1H, m), 7.65-7.69(1H, m), 7.95 (1H, d, J=2.20 Hz), 8.02 (2H, d, J=0.82 Hz), 8.24 (1H, s),8.46 (1H, d, J=1.92 Hz), 8.56 (1H, d, J=1.92 Hz), 8.97 (1H, s), 11.96(1H, br s); ESIMS found for C₁₈H₁₄N₆ m/z 315.05 (M+1).

(5-(5-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone 1055

Light yellow solid (5 mg, 0.011 mmol, 29.3% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.17 (3H, s), 2.34-2.40 (4H, m), 3.65-3.70 (4H, m), 3.90(3H, s), 7.51 (1H, dd, J=7.27, 2.06 Hz), 7.93 (1H, d, J=0.82 Hz), 8.13(1H, d, J=1.10 Hz), 8.18 (1H, d, J=2.47 Hz), 8.21 (1H, s), 8.24 (1H, s),8.42 (1H, d, J=1.92 Hz), 8.56 (1H, d, J=1.92 Hz), 8.78(1H, d, J=7.41Hz), 12.19 (1H, br s); ESIMS found for C₂₄H₂₄N₈O m/z 441.1 (M+1).

6-(5-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine1074

Tan solid (20 mg, 0.046 mmol, 39.4% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.71 (2H, qd, J=11.98, 3.84 Hz), 1.96 (2H, br dd, J=12.08, 2.20 Hz),1.99-2.06 (2H, m), 2.20 (3H, s), 2.85 (2H, br d, J=11.53 Hz), 3.89 (3H,s), 4.14-4.25 (1H, m), 7.74 (1H, d, J=8.51 Hz), 7.97-8.01 (3H, m), 8.21(1H, dd, J=8.51, 1.92 Hz), 8.24 (1H, s), 8.43 (1H, s), 8.46 (1H, d,J=1.92 Hz), 8.56 (1H, d, J=1.92 Hz), 8.59 (1H, d, J=1.65 Hz), 12.02 (1H,br s); ESIMS found for C₂₅H₂₆N₈ m/z 439.1 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole1081

Off-white solid (15 mg, 0.036 mmol, 50.1% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.60 (6H, d, J=6.86 Hz), 2.17 (3H, s), 2.26 (3H, s), 2.58(3H, s), 3.73 (3H, s), 4.80 (1H, spt, J=6.95 Hz), 7.29 (1H, d, J=12.08Hz), 7.68 (1H, s), 7.97 (1H, s), 8.03 (1H, d, J=1.92 Hz), 8.18 (1H, d,J=1.65 Hz), 12.00 (1H, br s); ESIMS found for C₂₄H₂₅FN₆ m/z 417.15(M+1).

3-(3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine1123

Beige solid (10 mg, 0.023 mmol, 26.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.63 (6H, br d, J=5.49 Hz), 2.43 (3H, br s), 2.60 (3H, br s), 2.90(2H, br s), 3.83 (2H, br s), 4.16 (2H, br s), 4.77-4.89 (1H, m), 7.31(1H, br d, J=11.25 Hz), 7.70 (1H, br s), 7.84 (1H, br s), 7.94 (1H, brs), 8.11 (1H, br s), 8.37 (1H, br s), 11.96 (1H, br s); ESIMS found forC₂₅H₂₆FN₇ m/z 444.15 (M+1).

5-(5-(5-Methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide1137

Beige solid (4 mg, 0.008 mmol, 10.5% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 2.38 (3H, s), 2.91 (2H, t, J=5.48 Hz), 3.94 (2H, s), 4.18 (2H, t,J=5.61 Hz), 7.39 (1H, dd, J=8.21, 4.65 Hz), 7.60 (1H, dd, J=7.26, 2.05Hz), 7.87 (1H, s), 8.26 (1H, dt, J=8.76, 1.78 Hz), 8.29 (1H, d, J=1.37Hz), 8.31 (2H, dd, J=8.76, 1.92 Hz), 8.48 (1H, d, J=1.92 Hz), 8.68 (1H,d, J=1.64 Hz), 8.77 (1H, s), 8.83 (1H, d, J=7.39 Hz), 8.96 (1H, d,J=2.46 Hz), 10.12 (1H, s), 12.30 (1H, br s); ESIMS found for C₂₇H₂₃N₉Om/z 490.1 (M+1).

6-(5-(5-Methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline1154

Light orange solid (4 mg, 0.011 mmol, 12.5% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.45 (3H, s), 2.91 (2H, br t, J=5.48 Hz), 3.86 (2H, s),4.18 (2H, br t, J=5.48 Hz), 7.93 (1H, s), 8.05 (1H, d, J=8.49 Hz), 8.19(1H, d, J=2.46 Hz), 8.37 (1H, d, J=1.92 Hz), 8.45 (1H, d, J=1.64 Hz),8.48 (1H, dd, J=8.90, 2.05 Hz), 8.52 (1H, d, J=1.92 Hz), 9.24 (1H, s),9.68 (1H, s), 12.18 (1H, br s); ESIMS found for C₂₂H₁₉N₇ m/z 382.1(M+1).

4-Fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole1166

Beige solid (14 mg, 0.032 mmol, 36.9% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.90 (2H, br dd, J=11.80, 2.47 Hz), 2.11-2.20 (2H, m), 2.28 (3H,s), 2.51-2.58 (2H, m), 2.61 (3H, s), 2.97 (2H, br d, J=11.25 Hz),4.32-4.44 (1H, m), 7.40(1H, dd, J=11.94, 0.96 Hz), 7.49-7.55 (1H, m),7.79 (1H, d, J=1.10 Hz), 8.05 (1H, s), 8.20 (1H, dt, J=7.96, 2.06 Hz),8.51 (1H, d, J=2.20 Hz), 8.60 (1H, dd, J=4.67, 1.65 Hz), 8.66 (1H, d,J=1.92 Hz), 9.00-9.06 (1H, m), 12.13 (1H, s); ESIMS found for C₂₆H₂₅FN₆m/z 441.2 (M+1).

N-(1-Methylpiperidin-4-yl)-5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide 1178

White solid (6 mg, 0.013 mmol, 13.2% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.57 (2H, qd, J=11.85, 3.43 Hz), 1.79 (2H, br d, J=10.70 Hz), 1.99(2H, br t, J=10.98 Hz), 2.18 (3H, s), 2.78 (2H, br d, J=11.25 Hz),3.73-3.84 (1H, m), 7.53-7.57 (2H, m), 7.94 (1H, d, J=7.96 Hz), 8.16-8.22(1H, m), 8.26 (1H, d, J=1.92 Hz), 8.53 (1H, d, J=1.37 Hz), 8.55 (1H, s),8.57 (1H, d, J=1.92 Hz), 8.62 (1H, br d, J=4.12 Hz), 8.66 (1H, d, J=1.92Hz), 8.76 (1H, d, J=7.14 Hz), 8.99 (1H, s), 12.39 (1H, br s); ESIMSfound for C₂₆H₂₅N₇O m/z 452.1 (M+1).

7-(5-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one1192

Beige solid (6 mg, 0.015 mmol, 59.5% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.58-1.68 (2H, m), 1.87 (2H, br d, J=12.90 Hz), 2.73 (2H, br d,J=12.62 Hz), 2.80 (2H, s), 2.90 (2H, br t, J=10.57 Hz), 7.44 (1H, s),7.53 (1H, br dd, J=7.55, 4.80 Hz), 7.57 (1H, br d, J=8.23 Hz), 7.78 (1H,br d, J=8.23 Hz), 8.17-8.26 (2H, m), 8.57 (1H, s), 8.60 (1H, br d,J=4.12 Hz), 8.63 (1H, s), 9.02 (1H, s), 12.33 (1H, br s); ESIMS foundfor C₂₅H₂₂N₄O₂ m/z 411.2 (M+1).

6-(5-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline 1194

Off-white solid (15 mg, 0.047 mmol, 28.1% yield). ¹H NMR (500 MHz,DMSO-d₆) δ ppm 7.50-7.58 (2H, m), 8.06 (1H, d, J=8.78 Hz), 8.18 (1H, s),8.23-8.27 (2H, m), 8.44 (1H, d, J=1.92 Hz), 8.50 (1H, dd, J=8.51, 1.10Hz), 8.61 (1H, dd, J=4.67, 1.65 Hz), 8.66 (1H, d, J=1.92 Hz), 8.76 (1H,d, J=1.92 Hz), 8.84 (1H, dd, J=4.12, 1.65 Hz), 9.07 (1H, dd, J=2.47,0.82 Hz), 12.23 (1H, s); ESIMS found for C₂₁H₁₄N₄ m/z 323.1 (M+1).

4-Methoxy-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl) quinazoline1197

White solid (6 mg, 0.017 mmol, 10.3% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 4.17 (3H, s), 7.50-7.57 (1H, m), 7.99 (1H, d, J=8.76 Hz), 8.19-8.23(2H, m), 8.40 (1H, d, J=1.64 Hz), 8.46 (1H, dd, J=8.62, 2.05 Hz), 8.58(1H, d, J=1.92 Hz), 8.60 (1H, dd, J=4.65, 1.37 Hz), 8.66 (1H, d, J=2.19Hz), 8.78 (1H, s), 9.02 (1H, d, J=1.92 Hz), 12.29 (1H, s); ESIMS foundfor C₂₁H₁₅N₅O m/z 354.05 (M+1).

4-(4-Methylpiperazin-1-yl)-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline 1198

Light orange solid (5 mg, 0.012 mmol, 22.2% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.17 (3H, s), 2.52 (4H, br s), 3.71-3.80 (4H, m),7.50-7.57 (1H, m), 7.88 (1H, d, J=8.76 Hz), 8.20 (1H, s), 8.22 (1H, dt,J=7.87, 1.95 Hz), 8.24 (1H, d, J=1.92 Hz), 8.31 (1H, dd, J=8.62, 2.05Hz), 8.57 (1H, d, J=2.19 Hz), 8.60-8.63 (2H, m), 8.66 (1H, d, J=2.19Hz), 9.02 (1H, d, J=2.46 Hz), 12.28 (1H, s); ESIMS found for C₂₅H₂₃N₇m/z 422.1 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole1207

White solid (8 mg, 0.020 mmol, 38.6% yield). ¹H NMR (500 MHz, DMSO-d₆) δppm 1.59 (6H, d, J=6.86 Hz), 2.51 (3H, br s), 2.58 (3H, s), 4.80 (1H,spt, J=7.02 Hz), 7.31-7.36 (2H, m), 7.69 (1H, d, J=1.37 Hz), 7.76 (1H,dd, J=7.68, 1.65 Hz), 8.03 (1H, d, J=2.74 Hz), 8.23 (1H, d, J=1.92 Hz),8.31 (1H, d, J=2.20 Hz), 8.49 (1H, dd, J=4.80, 1.78 Hz), 12.10 (1H, brs); ESIMS found for C₂₄H₂₂FN₅ m/z 400.2 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole1249

Beige solid (32 mg, 0.080 mmol, 72.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.59 (6H, d, J=6.86 Hz), 2.34 (3H, s), 2.58 (3H, s), 4.80 (1H,spt, J=6.93 Hz), 7.33 (1H, d, J=12.08 Hz), 7.38 (1H, d, J=4.94 Hz), 7.69(1H, s), 8.03 (1H, d, J=2.47 Hz), 8.23 (1H, d, J=1.92 Hz), 8.31 (1 d,J=1.92 Hz), 8.46 (1 d, J=5.21 Hz), 8.52 (1H, s), 12.10 (1H, s); ESIMSfound for C₂₄H₂₂FN₅ m/z 400.2 (M+1).

6-(5-(2,4-Dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole1291

White solid (20 mg, 0.048 mmol, 44.6% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.58 (6H, d, J=6.86 Hz), 2.06 (3H, s), 2.24 (3H, s), 2.58 (3H, s),4.78 (1H, spt, J=6.93 Hz), 7.21 (1H, d, J=5.21 Hz), 7.31 (1H, dd,J=11.94, 0.96 Hz), 7.65 (1H, d, J=1.10 Hz), 8.03 (1H, d, J=2.47 Hz),8.08 (1H, d, J=1.65 Hz), 8.10 (1H, d, J=1.92 Hz), 8.34 (1H, d, J=5.21Hz), 12.09 (1H, br s); ESIMS found for C₂₅H₂₄FN₅ m/z 414.2 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole 1333

White solid (10 mg, 0.021 mmol, 17.2% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.62 (6H, d, J=6.86 Hz), 2.23 (3H, s), 2.39-2.45 (4H, m), 2.59(3H, s), 3.51-3.57 (4H, m), 4.82 (1H, spt, J=6.93 Hz), 6.95 (1H, d,J=8.78 Hz), 7.36 (1H, d, J=12.08 Hz), 7.72 (1H, s), 7.93-7.97 (2H, m),8.33 (1H, d, J=2.20 Hz), 8.52 (2H, t, J=2.33 Hz), 11.98 (1H, s); ESIMSfound for C₂₈H₃₀FN₇ m/z 484.3 (M+1).

6-(5-(6-(4-Methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline 1362

Beige solid (30 mg, 0.071 mmol, 53.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 2.23 (3H, s), 2.42 (4H, t, J=5.08 Hz), 3.52-3.58 (4H, m), 6.96(1H, d, J=8.78 Hz), 7.53 (1H, dd, J=8.23, 4.12 Hz), 8.01 (1H, dd,J=8.78, 2.47 Hz), 8.05 (1H, d, J=8.78 Hz), 8.13 (1H, s), 8.23 (1H, dd,J=8.78, 1.92 Hz), 8.40 (1H, d, J=1.92 Hz), 8.49 (1H, d, J=7.68 Hz), 8.56(1H, d, J=2.20 Hz), 8.58 (1H, d, J=2.47 Hz), 8.61 (1H, d, J=2.20 Hz),8.84 (1H, dd, J=4.12, 1.65 Hz), 12.11 (1H, s); ESIMS found for C₂₆H₂₄N₆m/z 421.2 (M+1).

2-(5-(2-(4-Methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine 1370

Light orange solid (4 mg, 0.009 mmol, 23.7% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.28 (4H, br s), 3.56-3.68 (4H, m), 7.13 (1H, d, J=4.93Hz), 7.21 (1H, s), 7.74-7.81 (1H, m), 7.97 (1H, s), 8.23 (1H, br d,J=8.76 Hz), 8.23 (1H, s), 8.44 (1H, d, J=5.48 Hz), 8.68 (1H, d, J=1.92Hz), 8.73 (1H, d, J=1.92 Hz), 9.17 (1H, s), 12.49 (1H, br s); ESIMSfound for C₂₄H₂₂N₆S m/z 427.1 (M+1).

6-(5-(2-(4-Methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine 1372

Tan solid (4 mg, 0.010 mmol, 15.3% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 2.23 (3H, s), 2.42 (4H, t, J=4.94 Hz), 3.55-3.62 (4H, m), 7.11 (1H,dd, J=5.21, 1.10 Hz), 7.18 (1H, s), 7.58 (1H, d, J=1.10 Hz), 7.62-7.66(1H, m), 7.67-7.72 (1H, m), 8.01 (1H, s), 8.03 (1H, d, J=2.20 Hz), 8.20(1H, d, J=5.21 Hz), 8.63 (1H, d, J=1.92 Hz), 8.68 (1H, d, J=2.20 Hz),9.03 (1H, s), 12.16 (1H, s); ESIMS found for C₂₄H₂₃N₇ m/z 410.1 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole 1375

White solid (24 mg, 0.050 mmol, 48.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.63 (6H, d, J=6.86 Hz), 2.23 (3H, s), 2.41 (4H, t, J=4.94 Hz),2.60 (3H, s), 3.54-3.61 (4H, m), 4.84 (1H, spt, J=6.93 Hz), 7.07 (1H,dd, J=5.21, 1.10 Hz), 7.20 (1H, s), 7.35 (1H, d, J=11.80 Hz), 7.78 (1H,d, J=0.82 Hz), 8.00 (1H, s), 8.18 (1H, d, J=4.94 Hz), 8.51 (1H, d,J=1.92 Hz), 8.67 (1H, d, J=1.92 Hz), 12.10 (1H, s); ESIMS found forC₂₈H₃₀FN₇ m/z 484.3 (M+1).

6′-(5-(2-(4-Methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one 1398

Light yellow solid (20 mg, 0.041 mmol, 37.5% yield). ¹H NMR (500 MHz,DMSO-d₆) δ ppm 1.43 (3H, br d, J=12.08 Hz), 1.72 (5H, br s), 2.02-2.14(2H, m), 2.22 (3H, s), 2.39-2.45 (4H, m), 3.56-3.65 (4H, m), 7.08 (1H,dd, J=5.21, 1.37 Hz), 7.22 (1H, s), 7.67 (1H, d, J=7.68 Hz), 7.86 (1H,dd, J=7.82, 1.51 Hz), 8.02 (1H, d, J=0.82 Hz), 8.08 (1H, s), 8.19 (1H,d, J=5.21 Hz), 8.55 (1H, d, J=2.20 Hz), 8.67 (1H, d, J=2.20 Hz), 9.07(1H, s), 12.21 (1H, s); ESIMS found for C₃₀H₃₂N₆O m/z 493.2 (M+1).

6-(5-(2-(4-Methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline 1404

Off-white solid (15 mg, 0.036 mmol, 23.5% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.23 (3H, s), 2.42 (4H, t, J=4.94 Hz), 3.55-3.63 (4H, m),7.12 (1H, dd, J=5.21, 1.10 Hz), 7.19 (1H, s), 7.54 (1H, dd, J=8.23, 4.12Hz), 8.07 (1H, d, J=8.78 Hz), 8.16 (1H, s), 8.20 (1H, d, J=5.21 Hz),8.23 (1H, dd, J=8.78, 2.20 Hz), 8.41 (1H, d, J=1.92 Hz), 8.45-8.52 (1H,m), 8.69 (1H, d, J=2.20 Hz), 8.72 (1H, d, J=1.92 Hz), 8.85 (1H, dd,J=4.25, 1.78 Hz), 12.24 (1H, br s); ESIMS found for C₂₆H₂₄N₆ m/z 421.2(M+1).

6-(6-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline 1446

Beige solid (20 mg, 0.078 mmol, 10.9% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 7.28 (1H, d, J=8.23 Hz), 7.54 (1H, dd, J=8.23, 4.39 Hz), 8.05 (1H,d, J=8.78 Hz), 8.15 (1H, d, J=2.47 Hz), 8.17 (1H, dd, J=8.78, 2.20 Hz),8.33 (1H, d, J=1.92 Hz), 8.44 (1H, dd, J=8.64, 0.96 Hz), 8.58 (1H, d,J=8.23 Hz), 8.85 (1H, dd, J=4.25, 1.78 Hz), 12.29 (1H, br s); ESIMSfound for C₁₆H₁₀ClN₃ m/z 280.1 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole1459

White solid (14 mg, 0.043 mmol, 13.1% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 1.61 (6H, d, J=6.86 Hz), 2.55 (3H, s), 2.59 (3H, s), 4.81 (1H,spt, J=6.90 Hz), 7.06 (1H, d, J=8.23 Hz), 7.27 (1H, dd, J=12.08, 1.10Hz), 7.63 (1H, d, J=1.37 Hz), 7.83 (1H, d, J=2.47 Hz), 8.14 (1H, d,J=8.23 Hz), 11.71 (1H, br s); ESIMS found for C₁₉H₁₉FN₄ m/z 323.2 (M+1).

3,3-Dimethyl-5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one1481

White solid (36 mg, 0.124 mmol, 54.5% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.51 (6H, s), 2.55 (3H, s), 7.07 (1H, d, J=7.96 Hz), 7.62 (1H, d,J=7.96 Hz), 7.79 (1H, dd, J=7.96, 1.37 Hz), 7.90 (1H, s), 7.92 (1H, d,J=2.47 Hz), 8.25 (1H, d, J=8.23 Hz), 8.53 (1H, s), 11.84 (1H, br s);ESIMS found for C₁₈H₁₇N₃O m/z 292.1 (M+1).

6-(6-Methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline 1488

Pale yellow solid (52 mg, 0.201 mmol, 42.3% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.57 (3H, s), 7.10 (1H, d, J=8.23 Hz), 7.52 (1H, dd,J=8.23, 4.12 Hz), 8.00 (1H, d, J=2.20 Hz), 8.03 (1H, d, J=8.78 Hz), 8.17(1H, dd, J=8.78, 2.20 Hz), 8.30 (1H, d, J=1.92 Hz), 8.40-8.45 (2H, m),8.82 (1H, dd, J=4.12, 1.65 Hz), 11.85 (1H, br s); ESIMS found forC₁₇H₁₃N₃ m/z 260.1 (M+1).

5-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole1495

Off-white solid (5 mg, 0.017 mmol, 25.6% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 0.93-0.99 (4H, m), 2.11-2.20 (1H, m), 7.09 (1H, d, J=8.23Hz), 7.56-7.65 (2H, m), 7.68 (1H, d, J=2.74 Hz), 7.94 (1H, d, J=1.37Hz), 8.18 (1H, d, J=8.23 Hz), 8.28 (1H, s), 11.60 (1H, br s); ESIMSfound for C₁₈H₁₆N₄ m/z 289.05 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a] pyridine1498

Off-white solid (13.6 mg, 0.050 mmol, 45.2% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 0.92-1.01 (4H, m), 2.14-2.24 (1H, m), 7.14 (1H, d, J=8.23Hz), 7.55 (1H, d, J=1.10 Hz), 7.57-7.64 (2H, m), 7.81 (1H, d, J=2.47Hz), 7.99 (1H, s), 8.26 (1H, d, J=8.23 Hz), 8.91 (1H, d, J=1.37 Hz),11.76 (1H, br s); ESIMS found for C₁₇H₁₄N₄ m/z 275.1 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide 1499

Beige solid (5 mg, 0.013 mmol, 17.6% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 0.93-1.02 (4H, m), 2.14-2.23 (1H, m), 3.76 (2H, tdd, J=15.67, 15.67,5.61, 4.11 Hz), 6.18 (1H, tt, J=55.95, 3.90 Hz), 7.19 (1H, d, J=8.21Hz), 7.78 (1H, d, J=9.31 Hz), 7.89 (1H, dd, J=9.31, 1.92 Hz), 7.93 (1H,d, J=2.74 Hz), 8.12 (1H, d, J=8.21 Hz), 8.41 (1H, s), 8.88 (1H, t,J=6.02 Hz), 9.88 (1H, d, J=0.82 Hz), 11.88 (1H, br d, J=1.37 Hz); ESIMSfound for C₂₀H₁₇F₂N₅O m/z 382.2 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a] pyrimidine1500

Beige solid (20 mg, 0.073 mmol, 20.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 0.93-1.02 (4H, m), 2.15-2.25 (1H, m), 7.16 (1H, d, J=8.21 Hz),7.70 (1H, d, J=1.10 Hz), 7.92 (1H, d, J=1.37 Hz), 7.98 (1H, d, J=2.74Hz), 8.27 (1H, d, J=8.21 Hz), 8.96 (1H, d, J=2.74 Hz), 9.31 (1H, d,J=2.46 Hz), 11.89 (1H, br s); ESIMS found for C₁₆H₁₃N₅ m/z 276.1 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine1503

Brown solid (8.5 mg, 0.026 mmol, 25.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 0.92-0.99 (4H, m), 1.61 (6H, d, J=6.86 Hz), 2.13-2.22 (1H, m),2.63 (3H, s), 4.81 (1H, spt, J=6.93 Hz), 7.11 (1H, d, J=7.96 Hz), 7.83(1H, d, J=2.47 Hz), 8.12 (1H, d, J=8.23 Hz), 8.17 (1H, d, J=1.92 Hz),8.65 (1H, d, J=1.92 Hz), 11.76 (1H, br s); ESIMS found for C₂₀H₂₁N₅ m/z332.2 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine 1505

Beige solid (6 mg, 0.022 mmol, 30.2% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 0.94-1.01 (4H, m), 2.14-2.23 (1H, m), 7.13 (1H, d, J=8.21 Hz), 7.90(1H, dd, J=9.17, 0.96 Hz), 7.93 (1H, s), 8.07 (1H, dd, J=9.17, 1.78 Hz),8.24 (1H, d, J=8.21 Hz), 8.49 (1H, s), 9.17 (1H, dd, J=1.64, 0.82 Hz),11.89 (1H, br s); ESIMS found for C₁₆H₁₃N₅ m/z 276.1 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole1507

Off-white solid (20 mg, 0.069 mmol, 27.4% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 0.93-1.01 (4H, m), 2.15-2.23 (1H, m), 4.36 (3H, s), 7.15(1H, d, J=8.21 Hz), 7.78 (1H, dd, J=8.62, 1.51 Hz), 7.90 (1H, d, J=2.74Hz), 8.02 (1H, d, J=8.76 Hz), 8.04 (1H, s), 8.36 (1H, d, J=8.21 Hz),11.84 (1H, br s); ESIMS found for C₁₇H₁₅N₅ m/z 290.1 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b] pyridazine1508

Off-white solid (3.3 mg, 0.012 mmol, 23.4% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 0.94-1.01 (4H, m), 2.13-2.24 (1H, m), 7.20 (1H, d, J=7.96Hz), 7.68 (1H, d, J=1.10 Hz), 7.78 (1H, d, J=9.61 Hz), 8.05 (1H, d,J=9.61 Hz), 8.28 (1H, s), 8.33 (1H, s), 8.64 (1H, d, J=8.23 Hz), 12.08(1H, br s); ESIMS found for C₁₆H₁₃N₅ m/z 276.1 (M+1).

(R)-5-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide1513

Beige solid (11 mg, 0.027 mmol, 12.1% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 0.95-1.02 (4H, m), 1.39 (3H, d, J=7.12 Hz), 2.15-2.24 (1H, m),4.94 (1H, dq, J=15.61, 7.76 Hz), 7.23 (1H, d, J=8.21 Hz), 7.50 (1H, dd,J=7.26, 2.05 Hz), 8.11 (1H, d, J=2.19 Hz), 8.19 (1H, d, J=8.21 Hz),8.50-8.53 (2H, m), 8.64 (1H, s), 8.76 (1H, d, J=7.67 Hz), 12.04 (1H, brs); ESIMS found for C₂₁H₁₈F₃N₅O m/z 414.2 (M+1).

5-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide1514

Beige solid (50 mg, 0.121 mmol, 44.6% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 0.94-1.03 (4H, m), 1.58 (2H, qd, J=12.00, 3.70 Hz), 1.77-1.85 (2H,m), 1.91-2.01 (2H, m), 2.16-2.22 (1H, m), 2.18 (3H, s), 2.80 (2H, br d,J=11.50 Hz), 3.73-3.85 (1H, m), 7.22 (1H, d, J=8.21 Hz), 7.44 (1H, dd,J=7.39, 2.19 Hz), 7.94 (1H, d, J=7.67 Hz), 8.07 (1H, d, J=2.74 Hz), 8.19(1H, d, J=8.21 Hz), 8.53 (1H, d, J=1.64 Hz), 8.54 (1H, s), 8.67-8.73(1H, m), 12.00 (1H, br s); ESIMS found for C₂₄H₂₆N₆O m/z 415.2 (M+1).

(5-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone 1517

Off-white solid (4.5 mg, 0.011 mmol, 8.0% yield). ¹H NMR (500 MHz,DMSO-d₆) δ ppm 0.92-1.02 (4H, m), 2.16-2.21 (1H, m), 2.22 (3H, s),2.35-2.41 (4H, m), 3.65-3.72 (4H, m), 7.21 (1H, d, J=8.23 Hz), 7.45 (1H,dd, J=7.41, 1.92 Hz), 8.08 (1H, d, J=1.92 Hz), 8.14 (1H, d, J=1.65 Hz),8.17 (1H, d, J=8.23 Hz), 8.22 (1H, s), 8.74 (1H, d, J=7.41 Hz), 12.00(1H, br s); ESIMS found for C₂₃H₂₄N₆O m/z 401.3 (M+1).

5-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one 1522

Off-white solid (12 mg, 0.042 mmol, 36.8% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 0.92-1.00 (4H, m), 2.13-2.22 (1H, m), 4.42 (2H, s), 7.13(1H, d, J=8.23 Hz), 7.68 (1H, d, J=7.96 Hz), 7.79-7.83 (1H, m), 7.86(1H, d, J=2.20 Hz), 7.89 (1H, s), 8.23 (1H, d, J=8.23 Hz), 8.44 (1H, s),11.83 (1H, br s); ESIMS found for C₁₈H₁₅N₃O m/z 290.0 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one1526

Pale yellow solid (19.6 mg, 0.065 mmol, 28.4% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 0.92-1.00 (4H, m), 2.13-2.22 (1H, m), 2.97 (2H, t, J=6.59Hz), 3.40 (2H, td, J=6.52, 2.61 Hz), 7.12 (1H, d, J=8.23 Hz), 7.64 (1H,s), 7.68 (1H, dd, J=7.96, 1.37 Hz), 7.83 (1H, br s), 7.86 (1H, br d,J=11.25 Hz), 7.85 (1H, s), 8.22 (1H, d, J=8.23 Hz), 11.82 (1H, br s);ESIMS found for C₁₉H₁₇N₃O m/z 304.1 (M+1).

8-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one 1529

Off-white solid (18 mg, 0.056 mmol, 25.9% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 0.91-0.99(4H, m), 2.12-2.21 (1H, m), 3.34-3.40 (2H, m),4.31-4.37 (2H, m), 7.11 (1H, d, J=8.23 Hz), 7.31 (1H, d, J=1.37 Hz),7.48 (1H, dd, J=8.23, 1.65 Hz), 7.84 (1H, d, J=8.23 Hz), 7.87 (1H, d,J=1.92 Hz), 8.17 (1H, d, J=8.23 Hz), 8.25 (1H, br t, J=4.94 Hz), 11.83(1H, br s); ESIMS found for C₁₉H₁₇N₃O₂ m/z 320.1 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline 1530

White solid (13 mg, 0.046 mmol, 69.2% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 0.95-1.02 (4H, m), 2.20 (1H, quin, J=6.45 Hz), 7.16 (1H, d, J=8.23Hz), 7.52 (1H, dd, J=8.23, 4.12 Hz), 7.95 (1H, s), 8.02 (1H, d, J=8.78Hz), 8.16 (1H, dd, J=8.78, 2.20 Hz), 8.29 (1H, d, J=1.92 Hz), 8.38 (1H,d, J=8.23 Hz), 8.41-8.46 (1H, m), 8.82 (1H, dd, J=4.12, 1.65 Hz), 11.84(1H, br s); ESIMS found for C₁₉H₁₅N₃ m/z 286.1 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methoxyquinazoline1533

Brown solid ((4.3 mg, 0.014 mmol, 21.3% yield). ¹HNMR (499 MHz, DMSO-d₆)δ ppm 0.96-0.99 (4H, m), 2.14-2.24 (1H, m), 4.18 (3H, s), 7.17 (1H, d,J=7.96 Hz), 7.95 (1H, d, J=9.33 Hz), 7.99 (1H, s), 8.20 (1H, d, J=8.23Hz), 8.32-8.35 (2H, m), 8.76 (1H, s), 11.91 (1H, br s); ESIMS found forC₁₉H₁₆N₄O m/z 317.1 (M+1).

6-(6-Cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline1534

Off-white solid (4.7 mg, 0.012 mmol, 14.0% yield). ¹H NMR (500 MHz,DMSO-d₆) δ ppm 0.92-1.03 (4H, m), 2.15-2.23 (1H, m), 2.27 (3H, s),2.53-2.59 (4H, m), 3.72-3.83 (4H, m), 7.18 (1H, d, J=8.23 Hz), 7.85 (1H,d, J=8.78 Hz), 7.92 (1H, d, J=2.47 Hz), 8.11 (1H, d, J=1.92 Hz), 8.15(1H, d, J=8.23 Hz), 8.19 (1H, dd, J=8.64, 1.78 Hz), 8.60 (1H, s), 11.87(1H, br s); ESIMS found for C₂₃H₂₄N₆ m/z 385.2 (M+1).

6-(6-Cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole1543

White solid (36 mg, 0.099 mmol, 33.3% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 1.61 (6H, d, J=6.86 Hz), 1.81-1.92 (1H, m), 1.96-2.10 (1H, m),2.25-2.41 (4H, m), 2.56-2.62 (3H, m), 3.74 (1H, quin, J=8.58 Hz), 4.81(1H, spt, J=6.96 Hz), 7.06 (1H, d, J=7.96 Hz), 7.27 (1H, dd, J=12.08,1.10 Hz), 7.64 (1H, d, J=1.10 Hz), 7.85 (1H, d, J=2.47 Hz), 8.16 (1H, d,J=8.23 Hz), 11.83 (1H, br d, J=0.82 Hz); ESIMS found for C₂₂H₂₃FN₄ m/z363.2 (M+1).

6-(6-Cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridine1546

Off-white solid (55 mg, 0.159 mmol, 77.3% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.62 (6H, d, J=7.12 Hz), 1.81-1.93 (1H, m), 1.96-2.09(1H, m), 2.26-2.41 (4H, m), 2.59 (3H, s), 3.72 (1H, quin, J=8.83 Hz),4.78 (1H, spt, J=6.94 Hz), 7.03 (1H, d, J=8.21 Hz), 8.00 (1H, d, J=1.09Hz), 8.21 (1H, d, J=2.46 Hz), 8.68 (1H, d, J=8.21 Hz), 8.81 (1H, d,J=0.82 Hz), 11.81 (1H, br s); ESIMS found for C₂₁H₂₃N₅ m/z 346.2 (M+1).

6-(6-Cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine 1547

Beige solid (15 mg, 0.052 mmol, 31.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.82-1.92 (1H, m), 1.97-2.11 (1H, m), 2.25-2.39 (4H, m), 3.75 (1H,quin, J=8.69 Hz), 7.07 (1H, d, J=8.21 Hz), 7.91 (1H, dd, J=9.03, 0.82Hz), 8.01 (1H, d, J=2.74 Hz), 8.08 (1H, dd, J=9.31, 1.92 Hz), 8.28 (1H,d, J=7.94 Hz), 8.49 (1H, s), 9.19 (1H, dd, J=1.64, 0.82 Hz), 12.00 (1H,br s); ESIMS found for C₁₇H₁₅N₅ m/z 290.1 (M+1).

5-(6-Cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)pyrazolo[1,5-a]pyridine-3-carboxamide 1554

Beige solid (6 mg, 0.015 mmol, 7.6% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.82-1.94 (1H, m), 1.96-2.11 (1H, m), 2.27-2.40 (4H, m), 3.65-3.81(3H, m), 6.15 (1H, tt, J=56.20, 4.10 Hz), 7.16 (1H, d, J=8.21 Hz), 7.50(1H, dd, J=7.26, 2.05 Hz), 8.17 (1H, d, J=2.74 Hz), 8.24 (1H, d, J=7.94Hz), 8.53 (1H, d, J=1.37 Hz), 8.55-8.59 (2H, m), 8.74-8.80 (1H, m),12.15 (1H, br d, J=1.92 Hz); ESIMS found for C₂₁H₁₉F₂N₅O m/z 396.2(M+1).

5-(6-Cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide1556

Beige solid (50 mg, 0.117 mmol, 69.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.58 (2H, qd, J=11.96, 3.56 Hz), 1.76-1.84 (2H, m), 1.84-1.91 (1H,m), 1.95 (2H, td, J=11.77, 1.64 Hz), 1.99-2.09 (1H, m), 2.17 (3H, s),2.26-2.40 (4H, m), 2.79 (2H, br d, J=11.50 Hz), 3.71-3.83 (2H, m), 7.15(1H, d, J=8.21 Hz), 7.45 (1H, dd, J=7.26, 2.05 Hz), 7.95 (1H, d, J=7.94Hz), 8.14 (1H, d, J=1.92 Hz), 8.24 (1H, d, J=8.21 Hz), 8.54 (1H, d,J=1.92 Hz), 8.55 (1H, s), 8.71 (1H, d, J=7.39 Hz), 12.12 (1H, br s);ESIMS found for C₂₅H₂₈N₆O m/z 429.2 (M+1).

(5-(6-Cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone 1558

Beige solid (42 mg, 0.105 mmol, 64.7% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.53-1.61 (4H, m), 1.62-1.70 (2H, m), 1.81-1.92 (1H, m), 1.94-2.10(1H, m), 2.27-2.40 (4H, m), 3.60-3.68 (4H, m), 3.75 (1H, quin, J=8.69Hz), 7.14 (1H, d, J=8.21 Hz), 7.45 (1H, dd, J=7.26, 2.05 Hz), 8.13 (2H,t, J=2.19 Hz), 8.18 (1H, s), 8.21 (1H, d, J=8.21 Hz), 8.75 (1H, d,J=7.39 Hz), 12.11 (1H, br s); ESIMS found for C₂₄H₂₅N₅O m/z 400.2 (M+1).

8-(6-Cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one 1571

Brown solid (15 mg, 0.045 mmol, 5.4% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.80-1.92 (1H, m), 1.96-2.08 (1H, m), 2.25-2.39 (4H, m), 3.35-3.40(2H, m), 3.73 (1H, quin, J=8.62 Hz), 4.34 (2H, br t, J=4.24 Hz), 7.05(1H, d, J=8.21 Hz), 7.32 (1H, s), 7.49 (1H, br d, J=8.21 Hz), 7.85 (1H,br d, J=8.21 Hz), 7.94 (1H, d, J=1.92 Hz), 8.21 (1H, br d, J=8.21 Hz),8.25 (1H, br s), 11.95 (1H, br s); ESIMS found for C₂₀H₁₉N₃O₂ m/z 334.1(M+1).

6-(6-Cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline1577

Beige solid (30 mg, 0.073 mmol, 11.7% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.84-1.97 (3H, m), 2.05-2.12 (2H, m), 2.23 (3H, s), 2.28-2.43 (7H,m), 2.64 (2H, br s), 3.76 (1H, quin, J=8.69 Hz), 5.42 (1H, dt, J=7.19,3.66 Hz), 7.11 (1H, d, J=7.94 Hz), 7.94 (1H, d, J=8.76 Hz), 8.06 (1H,s), 8.24 (1H, d, J=8.21 Hz), 8.33 (1H, dd, J=8.62, 2.05 Hz), 8.36 (1H,d, J=1.92 Hz), 8.73 (1H, s), 12.05 (1H, br s); ESIMS found for C₂₅H₂₇N₅Om/z 414.1 (M+1).

5-(6-Cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide1598

Beige solid (18 mg, 0.041 mmol, 59.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.58 (2H, qd, J=11.91, 3.70 Hz), 1.65-1.74 (2H, m), 1.76-1.89 (6H,m), 1.95 (2H, td, J=11.70, 1.78 Hz), 2.02-2.11 (2H, m), 2.18 (3H, s),2.79 (2H, br d, J=11.77 Hz), 3.23-3.31 (1H, m), 3.73-3.84 (1H, m), 7.20(1H, d, J=8.21 Hz), 7.45 (1H, dd, J=7.26, 2.05 Hz), 7.94 (1H, d, J=7.67Hz), 8.12 (1H, d, J=2.46 Hz), 8.23 (1H, d, J=8.21 Hz), 8.54 (1H, d,J=1.37 Hz), 8.55 (1H, s), 8.71 (1H, dd, J=7.39, 0.82 Hz), 12.07 (1H, brs); ESIMS found for C₂₆H₃₀N₆O m/z 443.3 (M+1).

5-(6-(Cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide1640

Beige solid (18 mg, 0.041 mmol, 79.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.58 (2H, qd, J=12.05, 3.83 Hz), 1.74-1.87 (6H, m), 1.93-2.05 (4H,m), 2.18 (3H, s), 2.71-2.81 (3H, m), 2.92 (2H, d, J=7.67 Hz), 3.73-3.85(1H, m), 7.13 (1H, d, J=7.94 Hz), 7.45 (1H, dd, J=7.26, 2.05 Hz), 7.94(1H, d, J=7.67 Hz), 8.12 (1H, d, J=2.74 Hz), 8.22 (1H, d, J=8.21 Hz),8.53 (1H, d, J=1.92 Hz), 8.55 (1H, s), 8.71 (1H, d, J=7.39 Hz), 12.04(1H, br d, J=1.64 Hz); ESIMS found for C₂₆H₃₀N₆O m/z 443.25 (M+1).

6-(6-Methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine 1666

Beige solid (50 mg, 0.189 mmol, 21.5% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.90 (3H, s), 6.66 (1H, d, J=8.78 Hz), 7.55 (1H, d, J=1.10 Hz),7.57-7.64 (2H, m), 7.70 (1H, d, J=2.47 Hz), 7.97 (1H, s), 8.27-8.37 (1H,m), 8.90 (1H, t, J=1.24 Hz), 11.80(1H, br s); ESIMS found for C₁₅H₁₂N₄Om/z 265.0 (M+1).

6-(6-Methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine 1673

Beige solid (20 mg, 0.075 mmol, 26.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 3.90 (3H, s), 6.65 (1H, d, J=8.76 Hz), 7.81 (1H, d, J=1.64 Hz),7.89 (1H, dd, J=9.31, 0.82 Hz), 8.06 (1H, dd, J=9.31, 1.92 Hz), 8.29(1H, d, J=8.76 Hz), 8.48 (1H, s), 9.16 (1H, dd, J=1.78, 0.96 Hz), 11.91(1H, br s); ESIMS found for C₁₄H₁₁N₅O m/z 266.1 (M+1).

6-(6-Methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline 1698

Beige solid (15.0 mg, 0.054 mmol, 12.4% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 3.91 (3H, s), 6.68 (1H, d, J=8.51 Hz), 7.52 (1H, dd,J=8.23, 4.12 Hz), 7.83 (1H, d, J=2.20 Hz), 8.02 (1H, d, J=8.78 Hz), 8.15(1H, br d, J=8.78 Hz), 8.28 (1H, s), 8.38-8.49 (2H, m), 8.82 (1H, br d,J=3.02 Hz), 11.87 (1H, br s); ESIMS found for C₁₇H₁₃N₃O m/z 276.1 (M+1).

6-(6-(Difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine 1708

Off-white solid (65 mg, 0.217 mmol, 33.1% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 6.89 (1H, d, J=8.49 Hz), 7.70 (1H, t, J=73.50 Hz), 7.57(1H, d, J=1.09 Hz), 7.61-7.64 (2H, m), 7.89 (1H, d, J=2.46 Hz), 7.98(1H, d, J=0.82 Hz), 8.52 (1H, d, J=8.49 Hz), 8.95 (1H, t, J=1.37 Hz),12.12 (1H, br s); ESIMS found for C₁₅H₁₀F₂N₄O m/z 301.1 (M+1).

6-(6-Ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine 1750

Beige solid (30 mg, 0.108 mmol, 58.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.36 (3H, t, J=7.00 Hz), 4.35 (2H, q, J=6.95 Hz), 6.63 (1H, d,J=8.51 Hz), 7.55 (1H, d, J=1.10 Hz), 7.57-7.63 (2H, m), 7.68 (1H, d,J=2.74 Hz), 7.97 (1H, s), 8.30 (1H, d, J=8.51 Hz), 8.90 (1H, s), 11.75(1H, br s); ESIMS found for C₁₆H₁₄N₄O m/z 279.1 (M+1).

6-(6-Ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine 1757

Beige solid (15 mg, 0.054 mmol, 15.5% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.36 (3H, t, J=6.98 Hz), 4.35 (2H, q, J=6.94 Hz), 6.62 (1H, d,J=8.49 Hz), 7.80 (1H, d, J=2.46 Hz), 7.89 (1H, d, J=9.03 Hz), 8.05 (1H,dd, J=9.17, 1.78 Hz), 8.28 (1H, d, J=8.49 Hz), 8.48 (1H, s), 9.11-9.20(1H, m), 11.87 (1H, br s); ESIMS found for C₁₅H₁₃N₅O m/z 280.1 (M+1).

6-(6-Ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline 1782

Beige solid (20 mg, 0.069 mmol, 19.9% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.37 (3H, t, J=7.00 Hz), 4.36 (2H, q, J=7.04 Hz), 6.65 (1H, d,J=8.78 Hz), 7.51 (1H, dd, J=8.23, 4.12 Hz), 7.82 (1H, s), 8.01 (1H, d,J=8.78 Hz), 8.14 (1H, dd, J=8.92, 2.06 Hz), 8.27 (1H, d, J=1.92 Hz),8.42 (2H, d, J=8.51 Hz), 8.82 (1H, dd, J=4.25, 1.78 Hz), 11.84 (1H, brs); ESIMS found for C₁₈H₁₅N₃O m/z 290.1 (M+1).

(3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol1795

Off-white solid (10 mg, 0.030 mmol, 9.7% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.61 (6H, d, J=6.86 Hz), 2.59 (3H, s), 4.63 (2H, d,J=5.49 Hz), 4.82 (1H, spt, J=6.86 Hz), 5.34 (1H, t, J=5.76 Hz),7.26-7.33 (2H, m), 7.65 (1H, d, J=1.10 Hz), 7.88 (1H, d, J=1.37 Hz),8.26 (1H, d, J=8.23 Hz), 11.78 (1H, br s); ESIMS found for C₁₉H₁₉FN₄Om/z 339.2 (M+1).

5-(6-(Hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide 1809

Beige solid (15 mg, 0.039 mmol, 12.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 4.66 (2H, d, J=5.48 Hz), 5.40 (1H, t, J=5.89 Hz), 7.38-7.42 (1H,m), 7.41 (1H, d, J=8.21 Hz), 7.57 (1H, dd, J=7.26, 2.05 Hz), 8.21-8.25(2H, m), 8.30 (1H, dd, J=4.65, 1.37 Hz), 8.36 (1H, d, J=8.21 Hz), 8.58(1H, d, J=1.37 Hz), 8.77 (1H, s), 8.81-8.87 (1H, m), 8.93 (1H, d, J=2.19Hz), 10.13 (1H, s), 12.13 (1H, br s); ESIMS found for C₂₁H₁₆N₆O₂ m/z385.05 (M+1).

1-Methyl-N-(3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide1831

White solid (17 mg, 0.044 mmol, 46.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.60-1.71 (2H, m), 1.72-1.79 (2H, m), 1.85 (2H, td, J=11.66, 2.20Hz), 2.15 (3H, s), 2.42-2.49 (1H, m), 2.77-2.84 (2H, m), 4.17 (3H, s),7.58-7.66 (2H, m), 7.71 (1H, d, J=1.65 Hz), 7.93-7.99 (2H, m), 8.28-8.33(2H, m), 10.24 (1H, s), 11.56 (1H, s); ESIMS found for C₂₂H₂₄N₆O m/z389.1 (M+1).

N-(3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide1837

White solid (38 mg, 0.085 mmol, 76.7% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.61 (6H, d, J=6.86 Hz), 1.63-1.71(2H, m), 1.72-1.79 (2H, m), 1.85(2H, td, J=11.60, 2.06 Hz), 2.15 (3H, s), 2.59 (3H, s), 2.77-2.85 (2H,m), 4.82 (1H, spt, J=6.91 Hz), 7.28 (1H, dd, J=12.08, 1.10 Hz), 7.64(1H, d, J=1.10 Hz), 7.80 (1H, d, J=1.92 Hz), 7.97 (1H, br d, J=8.78 Hz),8.23 (1H, d, J=8.78 Hz), 10.24 (1H, s), 11.65 (1H, s); ESIMS found forC₂₅H₂₉FN₆O m/z 449.2 (M+1).

1-Methyl-N-(3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide1847

Beige solid (15 mg, 0.033 mmol, 21.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.60-1.71 (2H, m), 1.72-1.79 (2H, m), 1.86 (2H, td, J=11.64, 2.19Hz), 2.16 (3H, s), 2.43-2.49 (1H, m), 2.77-2.85 (2H, m), 7.41 (1H, dd,J=7.39, 1.92 Hz), 7.49-7.54 (1H, m), 8.02 (1H, d, J=8.76 Hz), 8.08-8.13(2H, m), 8.18 (1H, dt, J=8.21, 1.78 Hz), 8.35 (1H, d, J=8.76 Hz), 8.45(1H, s), 8.48 (1H, dd, J=4.65, 1.64 Hz), 8.75-8.80 (1H, m), 9.01 (1H,dd, J=2.46, 0.82 Hz), 10.30 (1H, s), 11.90 (1H, br s); ESIMS found forC₂₆H₂₅N₇O m/z 452.1 (M+1).

1-Methyl-N-(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide 1855

Off-white solid (25 mg, 0.058 mmol, 66.2% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.58-1.70 (2H, m), 1.71-1.79 (2H, m), 1.85 (2H, td,J=11.64, 2.19 Hz), 2.15 (3H, s), 2.23 (3H, s), 2.40-2.45 (4H, m),2.45-2.48 (1H, m), 2.76-2.84 (2H, m), 3.50-3.59 (4H, m), 7.03 (1H, dd,J=5.20, 1.10 Hz), 7.04 (1H, s), 7.97 (1H, br d, J=8.76 Hz), 7.99 (1H,s), 8.10 (1H, d, J=5.48 Hz), 8.31 (1H, d, J=8.76 Hz), 10.26 (1H, s),11.82 (1H, s); ESIMS found for C₂₄H₃₁N₇O m/z 434.15 (M+1).

N-(3-(4,4-Dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide1863

Off-white solid (8 mg, 0.019 mmol, 35.3% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.35 (6H, s), 1.60-1.70 (2H, m), 1.72-1.79 (2H, m),1.82-1.90 (2H, m), 2.16 (3H, s), 2.77-2.84 (2H, m), 3.19 (2H, d, J=2.74Hz), 7.67 (1H, s), 7.68 (1H, dd, J=7.80, 1.78 Hz), 7.86-7.91 (3H, m),7.98 (1H, br d, J=8.21 Hz), 8.28 (1H, d, J=9.03 Hz), 10.26 (1H, s),11.77 (1H, s); ESIMS found for C₂₅H₂₉N₅O₂ m/z 432.1 (M+1).

1-Methyl-N-(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide 1866

Yellow solid (25 mg, 0.065 mmol, 56.8% yield). ¹H NMR (500 MHz, DMSO-d₆)δ ppm 1.61-1.72 (2H, m), 1.73-1.80 (2H, m), 1.86 (2H, td, J=11.66, 2.20Hz), 2.16 (3H, s), 2.45-2.49 (1H, m), 2.77-2.85 (2H, m), 7.52 (1H, dd,J=8.23, 4.12 Hz), 7.98 (1H, d, J=1.37 Hz), 8.01-8.05 (2H, m), 8.18 (1H,dd, J=8.78, 2.20 Hz), 8.31 (1H, d, J=1.92 Hz), 8.44 (1H, dd, J=8.65,0.96 Hz), 8.50 (1H, d, J=8.78 Hz), 8.82 (1H, dd, J=4.12, 1.65 Hz), 10.29(1H, s), 11.79 (1H, s); ESIMS found for C₂₃H₂₃N₅O m/z 386.2 (M+1).

N-(3-(2-(4-Methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide 1897

Off-white solid (8 mg, 0.019 mmol, 35.1% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.24 (3H, s), 2.41-2.47 (4H, m), 3.53-3.59 (4H, m), 7.05(1H, dd, J=5.20, 1.37 Hz), 7.07 (1H, s), 7.91-7.95 (2H, m), 7.98 (1H, d,J=8.49 Hz), 8.06 (1H, s), 8.11 (1H, d, J=5.20 Hz), 8.39 (1H, d, J=8.76Hz), 8.74-8.78 (2H, m), 11.42 (1H, br s); ESIMS found for C₂₃H₂₃N₇O m/z414.1 (M+1).

N-(3-(Quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide 1908

Beige solid (20 mg, 0.055 mmol, 44.6% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 7.54 (1H, dd, J=8.23, 4.12 Hz), 7.91-7.97 (2H, m), 8.05 (1H, d,J=1.65 Hz), 8.07 (2H, d, J=1.10 Hz), 8.21 (1H, dd, J=8.78, 1.92 Hz),8.36 (1H, d, J=1.92 Hz), 8.45 (1H, d, J=7.41 Hz), 8.62 (1H, d, J=8.78Hz), 8.75-8.80 (2H, m), 8.84 (1H, dd, J=4.12, 1.65 Hz), 11.02 (1H, s),11.93 (1H, br s); ESIMS found for C₂₂H₁₅N₅O m/z 366.1 (M+1).

N-(3-(4-((1-Methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide 1913

Beige solid (25 mg, 0.052 mmol, 30.3% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.91-1.98 (2H, m), 2.05-2.13 (2H, m), 2.24 (3H, s), 2.36 (2H, brdd, J=3.56, 1.92 Hz), 2.62-2.69 (2H, m), 5.40-5.48 (1H, m), 7.92-7.95(2H, m), 7.96 (1H, d, J=8.76 Hz), 8.07 (1H, d, J=8.76 Hz), 8.09 (1H, d,J=2.19 Hz), 8.37 (1H, dd, J=8.76, 2.19 Hz), 8.39-8.43 (2H, m), 8.74 (1H,s), 8.77-8.80 (2H, m), 11.03 (1H, s), 12.00 (1H, br s); ESIMS found forC₂₇H₂₅N₇O₂ m/z 480.1 (M+1).

3-(3-(1-Methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine1930

Beige solid (20 mg, 0.040 mmol, 32.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 2.24 (3H, s), 2.46-2.49 (4H, m), 3.11-3.19 (4H, m), 3.92 (3H, s),6.48 (1H, dd, J=8.08, 2.05 Hz), 6.76 (1H, d, J=8.76 Hz), 7.09 (1H, t,J=8.08 Hz), 7.26 (2H, dd, J=7.39, 1.64 Hz), 7.47 (1H, t, J=2.05 Hz),7.81 (1H, d, J=2.46 Hz), 7.88 (2H, s), 8.15-8.18 (3H, m), 8.60-8.68 (1H,m), 8.91 (1H, s), 11.65 (1H, s); ESIMS found for C₂₉H₂₉N₉ m/z 504.15(M+1).

3-(Chroman-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-]pyridin-6-amine 1945

Brown solid (25 mg, 0.057 mmol, 16.5% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.90-2.00 (2H, m), 2.24 (3H, s), 2.45-2.49 (4H, m), 2.81 (2H, t,J=6.43 Hz), 3.09-3.18 (4H, m), 4.09-4.18 (2H, m), 6.46 (1H, dd, J=8.08,1.78 Hz), 6.65 (1H, d, J=8.49 Hz), 6.72-6.79 (1H, m), 7.07 (1H, t,J=8.08 Hz), 7.21 (1H, dd, J=7.94, 1.10 Hz), 7.32 (1H, d, J=2.46 Hz),7.32-7.35 (2H, m), 7.48 (1H, t, J=2.05 Hz), 8.00 (1H, d, J=8.49 Hz),8.80 (1H, s), 11.26 (1H, d, J=1.64 Hz); ESIMS found for C₂₇H₂₉N₅O m/z440.1 (M+1).

N-(3-(4-Methylpiperazin-1-yl)phenyl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine 1950

Beige solid (50 mg, 0.115 mmol, 52.9% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 2.24 (3H, s), 2.47-2.49 (4H, m), 3.11-3.20 (4H, m), 6.48 (1H, dd,J=8.10, 2.06 Hz), 6.75 (1H, d, J=8.78 Hz), 7.09 (1H, t, J=8.10 Hz), 7.23(1H, dd, J=7.96, 1.37 Hz), 7.49-7.54 (2H, m), 7.74 (1H, d, J=2.47 Hz),8.01 (1H, d, J=8.78 Hz), 8.15 (1H, dd, J=8.78, 1.92 Hz), 8.26 (1H, d,J=1.92 Hz), 8.32 (1H, d, J=8.51 Hz), 8.40-8.46 (1H, m), 8.81 (1H, dd,J=4.12, 1.65 Hz), 8.90 (1H, s), 11.58 (1H, d, J=1.92 Hz); ESIMS foundfor C₂₇H₂₆N₆ m/z 435.3 (M+1).

4-Fluoro-1-isopropyl-2-methyl-6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole1963

Off-white solid (26.0 mg, 0.067 mmol, 43.1% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.62 (6H, d, J=6.86 Hz), 2.59 (3H, s), 3.91 (3H, s), 4.82(1H, spt, J=6.91 Hz), 7.29 (1H, dd, J=12.08, 1.10 Hz), 7.48 (1H, d,J=8.51 Hz), 7.66 (1H, d, J=1.37 Hz), 7.86 (1H, d, J=2.47 Hz), 8.00 (1H,s), 8.22 (1H, d, J=8.51 Hz), 8.25 (1H, s), 11.84 (1H, s); ESIMS foundfor C₂₂H₂₁FN₆ m/z 389.2 (M+1).

5-(6-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide1976

Brown solid (10 mg, 0.022 mmol, 32.7% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.53-1.66 (2H, m), 1.78-1.87 (2H, m), 1.97 (2H, br t, J=10.54 Hz),2.18 (3H, s), 2.80 (2H, br d, J=11.50 Hz), 3.75-3.86 (1H, m), 3.92 (3H,s), 7.47 (1H, dd, J=7.39, 1.92 Hz), 7.57 (1H, d, J=8.49 Hz), 7.95 (1H,d, J=7.94 Hz), 8.01 (1H, s), 8.14 (1H, d, J=2.46 Hz), 8.27 (1H, s), 8.30(1H, d, J=8.21 Hz), 8.56 (2H, s), 8.73 (1H, d, J=7.39 Hz), 12.12 (1H, brs) ESIMS found for C₂₅H₂₆N₈O m/z 455.1 (M+1).

N-(1-Methylpiperidin-4-yl)-5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide2018

Beige solid (10 mg, 0.022 mmol, 32.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.59 (2H, qd, J=11.96, 3.83 Hz), 1.77-1.87 (2H, m), 1.93-2.02 (2H,m), 2.18 (3H, s), 2.80 (2H, br d, J=11.50 Hz), 3.74-3.88 (1H, m),7.39-7.46 (1H, m), 7.48-7.55 (3H, m), 7.91 (1H, d, J=8.49 Hz), 7.97 (1H,d, J=7.94 Hz), 8.13-8.19 (2H, m), 8.27 (1H, s), 8.43 (1H, d, J=8.49 Hz),8.57 (1H, s), 8.61 (1H, d, J=1.64 Hz), 8.75 (1H, d, J=7.39 Hz), 12.30(1H, br s); ESIMS found for C₂₇H₂₆N₆O m/z 451.25 (M+1).

(8-Methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)(3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone2041

Beige solid (8 mg, 0.020 mmol, 8.4% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.34-1.49 (1H, m), 1.54-1.69 (1H, m), 1.81-1.98 (3H, m), 2.18(3H,s), 2.93-3.05 (2H, m), 3.11-3.22 (1H, m), 3.42-3.56 (1H, m), 4.20-4.36(1H, m), 7.77 (1H, dd, J=5.48, 1.10 Hz), 7.88 (1H, s), 8.27 (1H, s),8.37 (1H, d, J=1.92 Hz), 8.44 (1H, d, J=2.46 Hz), 8.44 (1H, d, J=0.82Hz), 9.16 (1H, s), 12.55 (1H, br s); ESIMS found for C₂₂H₂₁N₅OS m/z404.1 (M+1).

6-(6-Cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrazine2042

Beige solid (15 mg, 0.052 mmol, 44.5% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.83-1.93 (1H, m), 1.96-2.10 (1H, m), 2.28-2.40 (4H, m), 3.75 (1H,quin, J=8.69 Hz), 7.08 (1H, d, J=8.21 Hz), 7.80 (1H, d, J=0.82 Hz), 8.00(1H, d, J=2.74 Hz), 8.12 (1H, s), 8.48 (1H, d, J=7.94 Hz), 9.05 (1H, d,J=1.37 Hz), 9.12 (1H, d, J=0.82 Hz), 11.92 (1H, br s); ESIMS found forC₁₇H₁₅N₅ m/z 290.1 (M+1).

3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylicacid 2043

Off-white solid (140 mg, 0.397 mmol, 88.0% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 1.62 (6H, d, J=6.86 Hz), 2.60 (3H, s), 4.81 (1H, spt,J=6.93 Hz), 7.30 (1H, dd, J=11.94, 0.96 Hz), 7.70 (1H, d, J=1.10 Hz),8.06 (1H, d, J=2.47 Hz), 8.74 (1H, d, J=1.65 Hz), 8.85 (1H, d, J=1.92Hz), 12.32 (1H, br s); ESIMS found for C₁₉H₁₇FN₄O₂ m/z 353.1 (M+1).

(3-(4-Fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)methanone2044

White solid (70.0 mg, 0.015 mmol, 12.5% yield). ¹HNMR (499 MHz, DMSO-d₆)δ ppm 1.37-1.51 (1H, m), 1.61 (6H, d, J=6.86 Hz), 1.88 (2H, br s), 2.16(3H, s), 2.59 (3H, s), 2.89-3.07 (2H, m), 3.08-3.20 (1H, m), 3.34-3.46(3H, m), 4.14-4.34 (1H, m), 4.81 (1H, spt, J=6.86 Hz), 7.25-7.31 (1H,m), 7.66 (1H, d, J=1.10 Hz), 8.03 (1H, s), 8.20 (1H, d, J=1.92 Hz), 8.30(1H, d, J=1.92 Hz), 12.19 (1H, br s); ESIMS found for C₂₆H₂₉FN₆O m/z461.2 (M+1).

4-Fluoro-1-isopropyl-6-(6-isopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-benzo[d]imidazole2045

White solid (30 mg, 0.086 mmol, 28.% yield). ¹H NMR (500 MHz, DMSO-d₆) δppm 1.30 (6H, d, J=6.86 Hz), 1.61 (6H, d, J=6.86 Hz), 1.70-1.81 (1H, m),2.59 (3H, s), 4.75-4.86 (1H, m), 7.04-7.13 (1H, m), 7.24-7.31 (1H, m),7.64 (1H, s), 7.83 (1H, t, J=2.20 Hz), 8.13-8.20 (1H, m), 11.75 (1H, brs); ESIMS found for C₂₁H₂₃FN₄ m/z 351.2 (M+1).

3-(3-(4-Methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile2046

Light yellow solid (42 mg, 0.109 mmol, 46.1% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.22 (3H, s), 2.39 (4H, t, J=4.94 Hz), 3.64-3.71 (4H, m),7.51 (1H, dd, J=7.27, 2.06 Hz), 8.13 (1H, d, J=1.37 Hz), 8.26 (1H, s),8.42 (1H, s), 8.72 (1H, d, J=1.92 Hz), 8.80-8.83 (2H, m), 12.84 (1H, brs); ESIMS found for C₂₁H₁₉N₇O m/z 386.1 (M+1).

(5-(5-Methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone2047

Light yellow solid (5 mg, 0.013 mmol, 5.9% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.21 (3H, s), 2.37 (4H, br t, J=4.94 Hz), 3.65-3.72 (4H,m), 3.91 (3H, s), 7.48 (1H, dd, J=7.14, 1.92 Hz), 7.82 (1H, d, J=2.74Hz), 8.10 (1H, d, J=1.65 Hz), 8.12 (1H, d, J=2.47 Hz), 8.17 (1H, d,J=2.47 Hz), 8.23 (1H, s), 8.77 (1H, d, J=7.14 Hz), 12.09 (1H, br s);ESIMS found for C₂₁H₂₂N₆O₂ m/z 391.1 (M+1).

3-([1,2,4]Triazolo[1,5-a]pyridin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-6-carboxamide2048

Beige solid (10 mg, 0.027 mmol, 18.0% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 1.59-1.71 (2H, m), 1.78-1.87 (2H, m), 2.02 (2H, br t, J=10.81 Hz),2.18 (3H, s), 2.75 (2H, br d, J=11.77 Hz), 3.73-3.85 (1H, m), 7.90 (1H,d, J=8.21 Hz), 7.94 (1H, d, J=9.31 Hz), 8.12 (1H, dd, J=9.31, 1.92 Hz),8.19 (1H, d, J=8.21 Hz), 8.28 (1H, s), 8.52 (1H, s), 8.55 (1H, d, J=8.21Hz), 9.26-9.31 (1H, m), 12.29 (1H, br s); ESIMS found for C₂₀H₂₁N₇O m/z376.2 (M+1).

(8-Methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone 2049

White solid (4 mg, 0.010 mmol, 9.2% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 1.34-1.51 (1H, m), 1.54-1.70 (1H, m), 1.83-1.95 (2H, m), 2.18(3H,s), 2.89-3.06 (2H, m), 3.11-3.23 (2H, m), 4.20-4.35 (1H, m), 6.58-6.66(1H, m), 7.30 (1H, dd, J=7.14, 1.92 Hz), 7.97 (1H, d, J=2.20 Hz), 8.04(1H, d, J=1.10 Hz), 8.21 (1H, d, J=2.20 Hz), 8.32 (1H, d, J=1.92 Hz),8.44 (1H, d, J=1.92 Hz), 8.68 (1H, d, J=7.14 Hz), 12.33 (1H, br s);ESIMS found for C₂₂H₂₂N₆O m/z 387.1 (M+1).

(4-Methylpiperazin-1-yl)(5-(5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone 2050

White solid (19.0 mg, 0.044 mmol, 37.7% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 2.22 (3H, s), 2.38 (4H, t, J=5.08 Hz), 3.65-3.72 (4H, m),7.48 (1H, dd, J=7.27, 2.06 Hz), 8.11 (1H, d, J=1.37 Hz), 8.14 (1H, dd,J=9.88, 2.74 Hz), 8.24 (1H, s), 8.33 (1H, s), 8.34 (1H, dd, J=2.47, 1.37Hz), 8.78 (1H, d, J=7.41 Hz), 12.39 (1H, br s); ESIMS found forC₂₁H₁₉F₃N₆O m/z 429.0 (M+1).

N-((6-(4-Methylpiperazin-1-yl)pyridin-3-yl)methyl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine2051

Beige solid (10 mg, 0.022 mmol, 9.7% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 2.20 (3H, s), 2.36 (4H, t, J=4.94 Hz), 3.38-3.43 (4H, m), 4.23 (2H,d, J=5.49 Hz), 5.16 (1H, t, J=5.35 Hz), 6.31 (1H, d, J=5.49 Hz), 6.73(1H, d, J=8.51 Hz), 7.35 (1H, d, J=1.65 Hz), 7.50-7.55 (2H, m), 7.89(1dd, J=8.51, 1.92 Hz), 7.92 (1H, d, J=5.21 Hz), 7.97 (1 d, J=1.92 Hz),8.01 (1H, d, J=8.51 Hz), 8.09 (1H, d, J=2.20 Hz), 8.28 (1H, d, J=7.68Hz), 8.85 (1H, dd, J=4.25, 1.78 Hz), 11.61 (1H, s); ESIMS found forC₂₇H₂₇N₇ m/z 450.25 (M+1).

N-((6-(1H-Imidazol-1-yl)pyridin-3-yl)methyl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine2052

Beige solid (10 mg, 0.024 mmol, 10.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 4.46 (2H, d, J=5.49 Hz), 5.50 (1H, t, J=5.76 Hz), 6.28 (1H, d,J=5.49 Hz), 7.12 (1H, s), 7.37 (1H, s), 7.49 (1H, dd, J=8.23, 4.12 Hz),7.74 (1H, d, J=8.23 Hz), 7.90-7.95 (3H, m), 7.98 (1H, dd, J=8.51, 2.20Hz), 8.02 (1H, d, J=1.65 Hz), 8.04 (1H, d, J=8.78 Hz), 8.32 (1H, d,J=7.41 Hz), 8.48 (1H, s), 8.49 (1H, d, J=1.92 Hz), 8.83 (1H, dd, J=4.12,1.65 Hz), 11.64 (1H, s); ESIMS found for C₂₅H₁₉N₇ m/z 418.15 (M+1).

6-(6-(Cyclopropylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline 2053

Beige solid (20 mg, 0.063 mmol, 20.8% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 0.32-0.40 (2H, m), 0.55-0.62 (2H, m), 1.24-1.36 (1H, m), 4.14 (2H,d, J=6.86 Hz), 6.68 (1H, d, J=8.51 Hz), 7.51 (1H, dd, J=8.23, 4.39 Hz),7.82 (1H, s), 8.01 (1H, d, J=8.78 Hz), 8.14 (1H, dd, J=8.92, 2.06 Hz),8.28 (1H, d, J=1.92 Hz), 8.39-8.47 (2H, m), 8.82 (1H, dd, J=4.12, 1.65Hz), 11.81 (1H, br s); ESIMS found for C₂₀H₁₇N₃O m/z 316.1 (M+1).

N-(Pyridin-4-yl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-6-carboxamide2054

Beige solid (15 mg, 0.041 mmol, 17.4% yield). ¹H NMR (499 MHz, DMSO-d₆)δ ppm 7.51-7.62 (1H, m), 7.93 (2H, br s), 8.07 (2H, br dd, J=19.76, 7.96Hz), 8.24 (1H, br d, J=8.78 Hz), 8.36-8.43 (2H, m), 8.47 (1H, br d,J=7.68 Hz), 8.52 (2H, br s), 8.78 (1H, br d, J=7.96 Hz), 8.86 (1H, brs), 10.77 (1H, br s), 12.37 (1H, br s); ESIMS found for C₂₂H₁₅N₅O m/z366.05 (M+1).

5-(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)thiazole 2055

Beige solid (5 mg, 0.015 mmol, 47.6% yield). ¹H NMR (499 MHz, DMSO-d₆) δppm 7.51-7.62 (1H, m), 7.93 (2H, br s), 8.07 (2H, br dd, J=19.76, 7.96Hz), 8.24 (1H, br d, J=8.78 Hz), 8.36-8.43 (2H, m), 8.47 (1H, br d,J=7.68 Hz), 8.52 (2H, br s), 8.78 (1H, br d, J=7.96 Hz), 8.86 (1H, brs), 10.77 (1H, br s), 12.37 (1H, br s); ESIMS found for C₁₉H₁₂N₄S m/z329.0 (M+1).

6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)-N-methylimidazo[1,2-a]pyridine-3-carboxamide2056

Off-white solid (14 mg, 0.035 mmol, 29.5% yield). ¹H NMR (499 MHz,DMSO-d₆) δ ppm 0.92-1.01 (4H, m), 2.13-2.24 (1H, m), 3.38 (3H, br s),4.03 (2H, td, J=15.33, 3.83 Hz), 6.35 (1H, tt, J=55.80, 3.90 Hz), 7.18(1H, d, J=8.21 Hz), 7.79 (1H, d, J=9.03 Hz), 7.86-7.89 (1H, m), 7.89(1H, d, J=2.74 Hz), 8.10 (1H, d, J=8.21 Hz), 8.17 (1H, s), 9.43 (1H, brs), 11.86 (1H, br d, J=1.37 Hz); ESIMS found for C₂₁H₁₉F₂N₅O m/z 396.2(M+1).

Example 9

Representative compounds were screened using the assay procedure forDYRK1A kinase activity as described below.

Each compound was dissolved in DMSO as a 10 mM stock and used to preparecompound source plates. Serial dilution (1:3, 11-point dose-responsecurves from 10 μM to 0.00016 μM) and compound transfer was performedusing the ECHO 550 (Labcyte, Sunnyvale, Calif.) into 1536-wellblack-walled round bottom plates (Corning).

The DYRK1A kinase assay was run using the Ser/Thr 18 peptide Z-lyteassay kit according to manufacturer's instructions (Life Technologies—aDivision of Thermo-Fisher). This is a non-radioactive assay usingfluorescence resonance energy transfer (FRET) between coumarin andfluorescein to detect kinase activity which is represented as a ratio ofcoumarin emission/fluorescein emission.

Briefly, recombinant DYRK1A kinase, ATP and Ser/Thr peptide 18 wereprepared in 1× Kinase buffer to final concentrations of 0.25 μg/mL, 15μM, and 4 μM respectively. The mixture was allowed to incubate with therepresentative compounds for one hour at room temperature. All reactionswere performed in duplicate. Unphosphorylated (“0% Control”) andphosphorylated (“100% control”) forms of Ser/Thr 18 served as controlreactions. Additionally, an 11-point dose-response curve ofStaurosporine (1 uM top) was run to serve as a positive compoundcontrol.

After incubation, Development Reagent A was diluted in DevelopmentBuffer then added to the reaction and allowed to further incubate forone hour at room temperature. The plate was read at Ex 400 Em 455 todetect the coumarin signal and Ex 400 Em 520 to measure the signal(EnVision Multilabel Plate Reader, PerkinElmer).

The Emission ratio (Em) was calculated as a ratio of the coumarin (C)emission signal (at 445 nm)/Fluorescein (F) emission signal (at 520 nm).The percent phosphorylation was then calculated using the followingformula: [1−((Em ratio×F100%)−C100%)/((C0%−C100%)+(Emratio×(F100%−F0%)))]. Dose-response curves were generated, andinhibitory concentration (IC₅₀) values were calculated using non-linearregression curve fit in the Dotmatics' Studies Software (BishopsStortford, UK).

Table 2 shows the measured activity for representative compounds ofFormula I as described herein.

TABLE 2 Compound EC₅₀ (μM) 2 0.050 3 0.006 4 0.007 5 0.010 7 0.201 80.007 9 0.019 10 0.014 11 0.012 12 0.003 13 0.021 14 0.001 18 0.017 200.010 21 0.016 23 0.002 24 0.001 25 0.001 26 0.058 27 0.002 28 0.019 290.010 30 0.013 31 0.004 32 0.151 34 0.002 35 0.002 36 0.002 37 0.001 380.002 41 0.002 42 0.002 43 0.001 44 0.001 45 0.001 46 0.005 47 0.002 480.001 49 0.001 50 0.001 51 0.001 52 0.002 53 0.007 54 0.018 55 0.004 560.007 57 0.003 58 0.012 59 0.081 60 0.006 61 0.004 62 0.005 63 0.005 640.006 65 0.007 67 0.019 69 0.073 70 0.013 72 0.091 76 0.031 78 0.006 790.024 80 0.031 82 0.006 83 0.029 84 0.003 85 0.025 86 0.007 87 0.002 880.003 89 0.001 90 0.003 91 0.003 92 0.005 93 0.004 95 0.002 96 0.001 970.002 98 0.002 99 0.002 100 0.006 101 0.006 102 0.002 103 0.001 1040.011 105 0.004 106 0.003 107 0.008 108 0.052 128 0.001 186 0.010 2150.012 226 0.036 257 0.016 280 0.004 325 0.002 367 0.002 409 0.013 4350.096 439 0.016 451 0.004 482 0.015 493 0.007 502 0.016 521 0.009 5350.002 573 0.010 577 0.003 619 0.000 648 0.002 661 0.002 703 0.003 7640.022 787 0.003 792 0.010 802 0.007 813 0.003 817 0.008 829 0.002 8710.002 913 0.004 955 0.020 997 0.006 1036 0.002 1055 0.009 1074 0.0191081 0.002 1123 0.004 1137 0.004 1154 0.010 1166 0.003 1178 0.006 11920.010 1194 0.000 1197 0.003 1198 0.003 1207 0.002 1249 0.002 1291 0.0071333 0.001 1362 0.001 1370 0.006 1372 0.001 1375 0.002 1384 0.001 13980.004 1404 0.001 1446 0.011 1459 0.004 1481 0.057 1488 0.002 1495 0.1051498 0.047 1499 0.001 1500 0.005 1502 0.005 1503 0.007 1505 0.100 15070.038 1508 0.029 1513 0.091 1514 0.005 1517 0.066 1522 0.012 1526 0.0101529 0.028 1530 0.024 1533 0.229 1534 0.012 1543 0.043 1546 2.053 15470.121 1554 0.008 1556 0.005 1558 0.291 1571 0.050 1577 0.214 1598 0.0041640 0.006 1666 0.018 1673 0.065 1698 0.007 1708 0.018 1750 0.009 17570.144 1782 0.015 1795 0.008 1809 0.003 1831 0.001 1837 0.001 1847 0.0011855 0.030 1863 0.005 1866 0.001 1897 0.051 1898 0.020 1899 0.014 19080.001 1913 0.005 1930 0.004 1945 0.125 1950 0.038 1963 0.045 1976 0.0102018 0.007 2041 0.115 2042 0.345 2043 0.036 2044 0.003 2045 0.036 20460.047 2047 0.032 2048 2.543 2049 0.045 2050 0.159 2051 0.037 2052 0.0342053 0.076 2054 0.051 2055 0.037 2056 0.005

Example 10

Representative compounds were screened using the assay procedure for tauphosphorylation activity described below.

HEK293T cells (ATCC, CRL3216) cultured in DMEM (Thermo FisherScientific, 10566024) supplemented with 10% FBS (Corning, 35-011-CV) andPenicillin/Streptomycin (Thermo Fisher Scientific, 15140163) were seededin a 75 cm² flask at 8.1×10⁶ cells/flask. The HEK293T cells were thentransiently transfected with 5 μg DYRK1A (NM_001396) human untaggedclone (OriGene, SC314641) and 2.5 μg MAPT (441 a.a. Tau gene)(NM_005910) human untagged clone (OriGene, TP313312) using Lipofectamine3000 (Thermo Fisher Scientific, L30000015) and incubated for 20-30 hoursin a humidified incubator at 37° C. and 5% CO₂. Post-incubation, HEK293Tcells transfected with the DYRK1A and MAPT expression vectors wereharvested and seeded in BioCoat poly-D lysine coated 96-well plates(Corning, 354461) at 3×10⁴ cells/well.

The above synthesized compounds were screened using the cell assayprocedure to assess decreased Tau phosphorylation at Thr212 (pThr212)described below.

Each compound was dissolved in DMSO (Sigma-Aldrich, D8418-100 mL) as a10 mM stock. 10 mM stocks were serially diluted 1:3, 10-pointdose-response curve and added to the cells with a final concentrationranging from 20 μM to 1.1 nM. Cell were treated with compounds induplicate and incubated for 18-24 hours in a humidified incubator at 37°C. and 5% CO₂.

Following the overnight compound treatment, cells were lysed with 1×Alpha Surefire Ultra Lysis Buffer (Perkin Elmer, ALSU-LB-100ML)complemented with 1× Halt Phosphatase Inhibitor Cocktail (Thermo FisherScientific, 78427) and 1× Halt Protease Inhibitor Cocktail (ThermoFisher Scientific, 78438). Lysates were spun down at 12,000 g for 10 minto remove any cellular debris and 5 μL of lysates were dispensed into a384-well Opti-Plate (Perkin Elmer, 6007290) for the measurement of Tauphosphorylation in the phosphoTau (Thr212) AlphaLISA assay. Donorantibody, biotinylated HT7Tau (Thermo Fisher Scientific, MN1000B), andacceptor antibody, pThr212Tau (Thermo Fisher Scientific, 44740G) wereboth added to the cell lysates at a final concentration of 3 nM andincubated for 1 hour at room temperature. Following incubation of thelysates with the donor and acceptor antibodies, anti-rabbit IgG(Fcspecific) AlphaLISA acceptor beads (Perkin Elmer, AL104C) were added ata 10 ug/mL final concentration and incubated for 1 hour at roomtemperature protected from light. Lastly, AlphaScreen streptavidin donorbeads (PerkinElmer, 6760002) were added at 40 ug/mL final concentrationand incubated for 1 hour at room temperature protected from light.Plates were read at Ex=665 nm, and Em=615 nm on the EnVision MultilabelPlate Reader (Perkin Elmer) phospho-Tau (Thr212) AlphaLISA signal wasused to plot, draw the curve fitting, and determine each compound's EC₅₀in Prism (GraphPad).

Table 3 shows the activity of representative compounds as providedherein.

TABLE 3 pTau (Thr212) Compound EC₅₀ (μM) 25 0.016 37 0.006 92 0.031 1070.396 215 0.258 817 0.210 1194 0.002 1488 0.039 1498 0.441 1502 0.9361508 0.321 1513 0.374 1514 0.082 1522 0.025 1526 0.073 1529 0.413 15300.393 1598 0.132 1640 0.199 1708 0.540 1750 0.210 1782 0.305 2018 0.0082046 0.622 2054 6.245

What is claimed is:
 1. A compound, or a pharmaceutically acceptable saltthereof, of Formula I:

wherein: R¹ is pyridinyl substituted with 1-4 R⁵; R² is selected fromthe group consisting of H, —OR⁷, 5-membered heteroaryl optionallysubstituted with 1-3 R⁸, and —NHR⁹. R³ is selected from the groupconsisting of H, CN, —CO₂H, unsubstituted —(C₁₋₉ alkyl), unsubstituted—(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉haloalkyl), —(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R¹¹,-(5-9 membered heteroaryl) optionally substituted with 1-10 R¹²; phenyloptionally substituted with 1-5 R¹³, —NHheteroaryl optionallysubstituted with 1-10 R¹⁴; —C(═O)NHR¹⁵, —NH(C═O)R¹⁶, and —C(═O)R¹⁷; R⁴is selected from the group consisting of H, halide, CN, —OR¹⁸, —CH₂OH,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), -(5-9membered heteroaryl) optionally substituted with 1-10 R¹⁹; phenyloptionally substituted with 1-5 R²⁰, —NHphenyl optionally substitutedwith 1-5 R²¹, —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R²², —C(═O)NHR²³, —NH(C═O)R²⁴, and —C(═O)R²⁵; with the proviso that atleast two of R², R³, and R⁴ are H; each R⁵ is independently selectedfrom the group consisting of —OR²⁶, -heterocyclyl optionally substitutedwith 1-10 R²⁷, and —NHheterocyclyl optionally substituted with 1-10 R²⁸;R⁷ is selected from the group consisting of H, unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl); each R⁸ is independently selectedfrom the group consisting of H, halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), andunsubstituted —(C₁₋₉ haloalkyl); R⁹ is —CH₂(6-membered heteroaryl)optionally substituted with 1-4 R³⁹; R¹⁰ is selected from the groupconsisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl); each R¹¹ is independently selected from the group consistingof halide, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR¹² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; each R¹³ isindependently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; each R¹⁴ isindependently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; R¹⁵ is selected fromthe group consisting of -heterocyclyl optionally substituted with 1-10R³⁷ and -heteroaryl optionally substituted with 1-10 R³⁹; R¹⁶ isselected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹; R¹⁷ is selected from the group consisting of -heterocyclyloptionally substituted with 1-10 R³⁷ and -heteroaryl optionallysubstituted with 1-10 R³⁹; R¹⁸ is selected from the group consisting ofunsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and—(CH₂)_(p)carbocyclyl optionally substituted with 1-12 R³⁸; each R¹⁹ isindependently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR²⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR²¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; each R²² isindependently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); R²³is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹; R²⁴ is selected from the group consisting of -heterocyclyloptionally substituted with 1-10 R³⁷ and -heteroaryl optionallysubstituted with 1-10 R³⁹; R²⁵ is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -heteroaryloptionally substituted with 1-10 R³⁹; each R²⁶ is unsubstituted —(C₁₋₉haloalkyl); each R²⁷ is independently selected from the group consistingof halide, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR²⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR³⁷ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸; each p is independently 0 or 1;and with the proviso that Formula I is not a structure selected from thegroup consisting of:


2. The compound of claim 1, wherein R¹ is 4-pyridine substituted withone R⁵.
 3. The compound of claim 1, wherein each R⁵ is independentlyselected from the group consisting of —OMe and -heterocyclyl optionallysubstituted with one R²⁷.
 4. The compound of claim 1, wherein R³ and R⁴are H and R² is selected from the group consisting of —OMe and a5-membered heteroaryl optionally substituted with one R⁸.
 5. Thecompound of claim 1, wherein R² and R⁴ are H and R³ is selected from thegroup consisting of -heterocyclyl optionally substituted with one R¹¹,-(5-6 membered heteroaryl) optionally substituted with 1-2 R¹²;—C(═O)NHR¹⁵, —NH(C═O)R¹⁶, and —C(═O)R¹⁷.
 6. The compound of claim 1,wherein R² and R³ are H and R⁴ is selected from the group consisting of-carbocyclyl, —C(═O)NHR²³, and —NH(C═O)R²⁴.
 7. A compound, or apharmaceutically acceptable salt thereof, of Formula Ia:

wherein: R¹ is selected from the heteroaryl group consisting of:

and optionally substituted with 1-10 R⁶; and

wherein a carbon atom on an aromatic ring of the heteroaryl form thebond with

each R⁶ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶; alternatively, twoR⁶ attached to the same carbon atom are taken together to form acarbonyl group; alternatively, two R⁶ attached to the same carbon atomare taken together to form a ring which is selected from the groupconsisting of -heterocyclyl optionally substituted with 1-10 R³⁷ and-carbocyclyl optionally substituted with 1-12 R³⁸; each R^(6a) isindependently selected from the group consisting of —OR^(29a), —CH₂OH,-heterocyclyl optionally substituted with 1-10 R³⁰, —CH₂N(R³⁴)₂,—C(═O)N(R³⁵)₂, and —C(═O)R³⁶; each R²⁹ is independently selected fromthe group consisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted—(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉haloalkyl), and -heterocyclyl optionally substituted with 1-10 R³⁷; eachR^(29a) is -heterocyclyl optionally substituted with 1-10 R³⁷; each R³⁰is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸; each R³¹ is independently selectedfrom the group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), andunsubstituted —(C₁₋₉ haloalkyl); each R³² is independently selected fromthe group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), andunsubstituted —(C₁₋₉ haloalkyl); each R³³ is independently selected fromthe group consisting of halide, —OR⁴⁵, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), and -heterocyclyl optionallysubstituted with 1-10 R³⁷; each R³⁴ are independently selected from thegroup consisting of H, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl); each R³⁵ are independently selected from the groupconsisting of H, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl); —(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰,and -heteroaryl optionally substituted with 1-10 R³⁹; each R³⁶ is-heterocyclyl optionally substituted with 1-10 R⁴¹; each R³⁷ isindependently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸; each R⁴⁰ is independently selectedfrom the group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), —(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyloptionally substituted with 1-12 R³⁸, and —(CH₂)_(p)heteroaryloptionally substituted with 1-10 R³⁹; each R⁴¹ is independently selectedfrom the group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), -carbocyclyl optionally substitutedwith 1-12 R³⁸, and -heterocyclyl optionally substituted with 1-10 R³⁷;alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸; each R⁴² is independently selectedfrom the group consisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted—(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl); each R⁴⁵ is independently selected from the group consistingof unsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; each n isindependently 0 to 3; each m is independently 1 to 6; each p isindependently 0 or 1; and with the proviso that Formula Ia is not astructure selected from the group consisting of:


8. The compound of claim 7, wherein R¹ is selected from the groupconsisting of:

optionally substituted with 1-2 R⁶.
 9. The compound of claim 8, whereineach R⁶ is independently selected from the group consisting ofunsubstituted —(C₁₋₃ alkyl), -heterocyclyl optionally substituted withone R³⁰, -(5-6 membered heteroaryl) optionally substituted with 1-2 R³²,and —C(═O)NHR³⁵.
 10. A compound, or a pharmaceutically acceptable saltthereof, of Formula Ib:

R¹ is 7-14-membered heteroaryl optionally substituted with 1-10 R⁶; withthe proviso that when the heteroaryl is selected from the groupconsisting of

that the 2-position is substituted with R⁴²; wherein a carbon atom on anaromatic ring of the heteroaryl form the bond with

R² is selected from the group consisting of H, —OR⁷, 5-memberedheteroaryl optionally substituted with 1-3 R⁸, and —NHR⁹; R⁴ is selectedfrom the group consisting of H, halide, CN, —OR¹⁸, —CH₂OH, unsubstituted—(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉alkynyl), unsubstituted —(C₁₋₉ haloalkyl), -(5-9 membered heteroaryl)optionally substituted with 1-10 R¹⁹; phenyl optionally substituted with1-5 R²⁰, —NHphenyl optionally substituted with 1-5 R²¹,—(CH₂)_(p)carbocyclyl optionally substituted with 1-12 R²², —C(═O)NHR²³,—NH(C═O)R²⁴, and —C(═O)R²⁵; with the proviso that one of R² and R⁴ is Hand the other of R² and R⁴ is not H; each R⁶ is independently selectedfrom the group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹, —CH₂OH, -heterocyclyl optionallysubstituted with 1-10 R³⁰, —NHheterocyclyl optionally substituted with1-10 R³¹, -heteroaryl optionally substituted with 1-10 R³²;—NHheteroaryl optionally substituted with 1-10 R³³; —NHCH₂heteroaryloptionally substituted with 1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and—C(═O)R³⁶; alternatively, two R⁶ attached to the same carbon atom aretaken together to form a carbonyl group; alternatively, two R⁶ attachedto the same carbon atom are taken together to form a ring which isselected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -carbocyclyl optionally substituted with1-12 R³⁸; R⁷ is selected from the group consisting of H, unsubstituted—(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); each R⁸ is independentlyselected from the group consisting of H, halide, unsubstituted —(C₁₋₉alkyl), unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),and unsubstituted —(C₁₋₉ haloalkyl); R⁹ is —CH₂(6-membered heteroaryl)optionally substituted with 1-4 R³⁹; R¹⁸ is selected from the groupconsisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉haloalkyl), and —(CH₂)_(p)carbocyclyl optionally substituted with 1-12R³⁸; each R¹⁹ is independently selected from the group consisting ofhalide, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR²⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR²¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; each R²² isindependently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); R²³is selected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹; R²⁴ is selected from the group consisting of -heterocyclyloptionally substituted with 1-10 R³⁷ and -heteroaryl optionallysubstituted with 1-10 R³⁹; R²⁵ is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -heteroaryloptionally substituted with 1-10 R³⁹; each R²⁹ is independently selectedfrom the group consisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted—(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉haloalkyl), and -heterocyclyl optionally substituted with 1-10 R³⁷; eachR³⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸; each R³¹ is independently selectedfrom the group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), andunsubstituted —(C₁₋₉ haloalkyl); each R³² is independently selected fromthe group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), andunsubstituted —(C₁₋₉ haloalkyl); each R³³ is independently selected fromthe group consisting of halide, —OR⁴⁵, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), and -heterocyclyl optionallysubstituted with 1-10 R³⁷; each R³⁴ are independently selected from thegroup consisting of H, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl); each R³⁵ are independently selected from the groupconsisting of H, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl); —(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰,and -heteroaryl optionally substituted with 1-10 R³⁹; each R³⁶ is-heterocyclyl optionally substituted with 1-10 R⁴¹; each R³⁷ isindependently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸; each R⁴⁰ is independently selectedfrom the group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), —(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyloptionally substituted with 1-12 R³⁸, and —(CH₂)_(p)heteroaryloptionally substituted with 1-10 R³⁹; each R⁴¹ is independently selectedfrom the group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), -carbocyclyl optionally substitutedwith 1-12 R³⁸, and -heterocyclyl optionally substituted with 1-10 R³⁷;alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸; each R⁴² is independently selectedfrom the group consisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted—(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl); each R⁴⁵ is independently selected from the group consistingof unsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; each m isindependently 1 to 6; each p is independently 0 or 1; and with theproviso that Formula Ib is not a structure selected from the groupconsisting of:


11. The compound of claim 10, wherein R¹ is selected from the groupconsisting of:

optionally substituted with 1-2 R⁶.
 12. The compound claim 11, whereineach R⁶ is independently selected from the group consisting ofunsubstituted —(C₁₋₃ alkyl), -heterocyclyl optionally substituted withone R³⁰, -(5-6 membered heteroaryl) optionally substituted with 1-2 R³²,and —C(═O)NHR³⁵.
 13. The compound of claim 12, wherein R⁴ is H and R² isselected from the group consisting of —OMe and a 5-membered heteroaryloptionally substituted with one R⁸.
 14. The compound of claim 12,wherein R² is H and R⁴ is selected from the group consisting of-carbocyclyl, —C(═O)NHR²³, and —NH(C═O)R²⁴.
 15. A compound, or apharmaceutically acceptable salt thereof, of Formula Ie:

wherein: R¹ is selected from the heteroaryl group consisting of:

and optionally substituted with 1-10 R⁶; and

with the proviso that when R¹ is

R³ is not halide or methyl; wherein a carbon atom on an aromatic ring ofthe heteroaryl form the bond with

R³ is selected from the group consisting of halide, CN, —CO₂H, —OR¹⁰,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉alkynyl), unsubstituted —(C₁₋₉haloalkyl),—(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R¹¹, -(5-9membered heteroaryl) optionally substituted with 1-10 R¹²; phenyloptionally substituted with 1-5 R¹³, —NHheteroaryl optionallysubstituted with 1-10 R¹⁴; —C(═O)NHR¹⁵, —NH(C═O)R¹⁶, and —C(═O)R¹⁷; eachR⁶ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉alkynyl), unsubstituted —(C₁₋₉haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶; alternatively, twoR⁶ attached to the same carbon atom are taken together to form acarbonyl group; alternatively, two R⁶ attached to the same carbon atomare taken together to form a ring which is selected from the groupconsisting of -heterocyclyl optionally substituted with 1-10 R³⁷ and-carbocyclyl optionally substituted with 1-12 R³⁸; each R^(6a) isindependently selected from the group consisting of halide,unsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), —OR²⁹,—CH₂OH, -heterocyclyl optionally substituted with 1-10 R³⁰,—NHheterocyclyl optionally substituted with 1-10 R³¹, -heteroaryloptionally substituted with 1-10 R³²; —NHheteroaryl optionallysubstituted with 1-10 R³³; —NHCH₂heteroaryl optionally substituted with1-10 R³³; —CH₂N(R³⁴)₂, —C(═O)N(R³⁵)₂, and —C(═O)R³⁶; each R^(6b) isindependently selected from the group consisting of —OR²⁹, —CH₂OH,-heterocyclyl optionally substituted with 1-10 R³⁰, —CH₂N(R³⁴)₂,—C(═O)N(R³⁵)₂, and —C(═O)R³⁶; R¹⁰ is selected from the group consistingof unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR¹¹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR¹² is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; each R¹³ isindependently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; each R¹⁴ isindependently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; R¹⁵ is selected fromthe group consisting of -heterocyclyl optionally substituted with 1-10R³⁷ and -heteroaryl optionally substituted with 1-10 R³⁹; R¹⁶ isselected from the group consisting of -heterocyclyl optionallysubstituted with 1-10 R³⁷ and -heteroaryl optionally substituted with1-10 R³⁹; R¹⁷ is selected from the group consisting of -heterocyclyloptionally substituted with 1-10 R³⁷ and -heteroaryl optionallysubstituted with 1-10 R³⁹; each R²⁹ is independently selected from thegroup consisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉haloalkyl), and -heterocyclyl optionally substituted with 1-10 R³⁷; eachR³⁰ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl);alternatively, two R³⁰ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸; each R³¹ is independently selectedfrom the group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), andunsubstituted —(C₁₋₉ haloalkyl); each R³² is independently selected fromthe group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), andunsubstituted —(C₁₋₉ haloalkyl); each R³³ is independently selected fromthe group consisting of halide, —OR⁴⁵, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), and -heterocyclyl optionallysubstituted with 1-10 R³⁷; each R³⁴ are independently selected from thegroup consisting of H, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl); each R³⁵ are independently selected from the groupconsisting of H, unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl); —(CH₂)_(p)heterocyclyl optionally substituted with 1-10 R⁴⁰,and -heteroaryl optionally substituted with 1-10 R³⁹; each R³⁶ is-heterocyclyl optionally substituted with 1-10 R⁴¹; each R³⁷ isindependently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR³⁸ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉ haloalkyl); eachR³⁹ is independently selected from the group consisting of halide,unsubstituted —(C₁₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl),-heterocyclyl optionally substituted with 1-10 R³⁷, and -heteroaryloptionally substituted with 1-10 R³⁸; each R⁴⁰ is independently selectedfrom the group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), —(CH₂)_(m)OMe, —(CH₂)_(p)carbocyclyloptionally substituted with 1-12 R³⁸, and —(CH₂)_(p)heteroaryloptionally substituted with 1-10 R³⁹; each R⁴¹ is independently selectedfrom the group consisting of halide, unsubstituted —(C₁₋₉ alkyl),unsubstituted —(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl),unsubstituted —(C₁₋₉ haloalkyl), -carbocyclyl optionally substitutedwith 1-12 R³⁸, and -heterocyclyl optionally substituted with 1-10 R³⁷;alternatively, two R⁴¹ attached to the same carbon atom are takentogether to form a ring which is selected from the group consisting of-heterocyclyl optionally substituted with 1-10 R³⁷ and -carbocyclyloptionally substituted with 1-12 R³⁸; each R⁴² is independently selectedfrom the group consisting of unsubstituted —(C₁₋₉ alkyl), unsubstituted—(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted—(C₁₋₉haloalkyl); each R⁴³ is H; each R⁴⁴ is independently selected fromthe group consisting of H, unsubstituted —(C₂₋₉ alkyl), unsubstituted—(C₂₋₉ alkenyl), unsubstituted —(C₂₋₉ alkynyl), and unsubstituted —(C₁₋₉haloalkyl); each R⁴⁵ is independently selected from the group consistingof unsubstituted —(C₂₋₉ alkyl), unsubstituted —(C₂₋₉ alkenyl),unsubstituted —(C₂₋₉ alkynyl), unsubstituted —(C₁₋₉ haloalkyl), and-heterocyclyl optionally substituted with 1-10 R³⁷; each n isindependently 0 to 6; each m is independently 1 to 6; each p isindependently 0 or 1; and with the proviso that Formula Ie is not astructure selected from the group consisting of:


16. The compound of claim 15, wherein R¹ is selected from the groupconsisting of:

optionally substituted with 1-2 R⁶.
 17. The compound of claim 16,wherein each R⁶ is independently selected from the group consisting ofunsubstituted —(C₁₋₃ alkyl), -heterocyclyl optionally substituted withone R³⁰, -(5-6 membered heteroaryl) optionally substituted with 1-2 R³²,and —C(═O)NHR³⁵.
 18. The compound of claim 17, wherein R³ is selectedfrom the group consisting of -heterocyclyl optionally substituted withone R¹¹, -(5-6 membered heteroaryl) optionally substituted with 1-2 R¹²;—C(═O)NHR¹⁵, —NH(C═O)R¹⁶, and —C(═O)R¹⁷.
 19. The compound according toclaim 1, wherein the compound of Formula I is selected from the groupconsisting of:3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[68];4-(1-methyl-1H-pyrazol-4-yl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[175];5-methyl-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[301];5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[343];5-(4-methylpiperazin-1-yl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[385];5-((4-methylpiperazin-1-yl)methyl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[427];3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[469];(4-methylpiperazin-1-yl)(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[511];(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[553];(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[595];1-methyl-N-(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[637];3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[679];3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[721];N-(5-fluoropyridin-3-yl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[763];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[805];N-(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[847];N,3-bis(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[889];3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridine[931];3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridine[973];5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1015];5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1060];3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine[1099]; and5-methyl-3-(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine[1141];3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1183];3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1225];3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1267];5-(2,4-dimethylpyridin-3-yl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1309];5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1351];3,5-bis(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1393];6-chloro-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1435];6-methyl-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1477]; 5-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1522];6-cyclobutyl-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1561];6-cyclopentyl-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1603];6-(cyclobutylmethyl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1645];6-methoxy-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1687];6-(difluoromethoxy)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1729];6-ethoxy-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1771];(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1813];1-methyl-N-(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1855];N-(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1897];N-(3-(4-methylpiperazin-1-yl)phenyl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1939];6-(1-methyl-1H-pyrazol-4-yl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1981]; and3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-6-phenyl-1H-pyrrolo[2,3-b]pyridine[2023]; or a pharmaceutically acceptable salt thereof.
 20. The compoundaccording to claim 7, wherein the compound of Formula Ia is selectedfrom the group consisting of: 1H,1′H-3,4′-bipyrrolo[2,3-b]pyridine [2];2-(1H-pyrrolo[2,3-b]pyridin-3-yl)thiazolo[5,4-b]pyridine [4];2-(1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine [5];1H,1′H-2,3′-bipyrrolo[2,3-b]pyridine [6];2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one[8];6,6-dimethyl-2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydro-4H-imidazo[1,5-b]pyrazol-4-one[9];7-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[10];2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one[11]; 6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine [12];8-fluoro-2-methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[13];N-(1-methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[14];N-methyl-N-(1-methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[15];N-(2,2-difluoroethyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[16];N-(2,2-difluoroethyl)-N-methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[17];1-(6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)-N,N-dimethylmethanamine[18]; 6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine [19];6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrazine [20];(6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrazin-3-yl)(4-methylpiperazin-1-yl)methanone[21];4-fluoro-1-isopropyl-2-methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[22];4-fluoro-2-methyl-1-(piperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[23];4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[24];1-isopropyl-2-methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[25];3-isopropyl-2-methyl-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3H-imidazo[4,5-b]pyridine[26];3-isopropyl-2-methyl-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3H-imidazo[4,5-b]pyridine[27];2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-7,8-dihydro-6H-pyrrolo[2′,1′:2,3]imidazo[4,5-b]pyridine[28]; 6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[29]; 7-(1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[30];3-methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridine[32]; 6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine [33];3-methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine [34];(6-(1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazin-3-yl)methanol[35]; 3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine [36];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[37];3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[38];N-(2,2-difluoroethyl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[39];(R)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[40];N-((3-fluoroazetidin-3-yl)methyl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[41];N-((3-fluoro-1-methylazetidin-3-yl)methyl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[42];N-((3R,4R)-3-fluoropiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[43];N-((3R,4R)-3-fluoro-1-methylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[44];N-(1-methylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[45];N-methyl-N-(1-methylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[46];N-(1-cyclopropylpiperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[47];N-(1-(cyclopropylmethyl)piperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[48];N-(1-(2,2-difluoropropyl)piperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[49];N-(1-(2-methoxyethyl)piperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[50];N-(1-(pyridin-2-ylmethyl)piperidin-4-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[51];N-(pyridin-3-yl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[52];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[53];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-(4-methylpiperazin-1-yl)piperidin-1-yl)methanone[54];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[55];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-cyclopropylpiperazin-1-yl)methanone[56];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4,7-diazaspiro[2.5]octan-7-yl)methanone[57];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)methanone[58];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[59];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[60];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(2,6-diazaspiro[3.3]heptan-2-yl)methanone[61];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(6-methyl-2,6-diazaspiro[3.3]heptan-2-yl)methanone[62];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone[63];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone[64]; 5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyrimidine [65];3-(3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)-1H-pyrrolo[2,3-b]pyridine[72];6-(1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[73];1′-methyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[74]; 5-(1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one [75];3,3-dimethyl-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one [77];6′-(1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[78]; 3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridine [79];2,2-dimethyl-7-(1H-pyrrolo[2,3-b]pyridin-3-yl)chroman-4-one [80];6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one [81];4,4-dimethyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[82];7-(1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[83];8-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[84];4-methyl-8-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[85];9-fluoro-8-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[86];(6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinolin-4-yl)(4,7-diazaspiro[2.5]octan-7-yl)methanone[88];N-(1-methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline-4-carboxamide[89]; 6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [90];2-((1-methylpiperidin-4-yl)oxy)-7-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[91];N-(1-methylpiperidin-4-yl)-7-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxalin-2-amine[92]; 6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [93];4-methoxy-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [94];4-(4-methylpiperazin-1-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[95];6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4,7-diazaspiro[2.5]octan-7-yl)quinazoline[96];6-(1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(5,8-diazaspiro[3.5]nonan-8-yl)quinazoline[97];9-(6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-yl)-6,9-diazaspiro[4.5]decane[98];4-((1-methylpiperidin-4-yl)oxy)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[99];N-(1-methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[100];N-(6-methoxypyridin-3-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[101];N-(6-((1-methylpiperidin-4-yl)oxy)pyridin-3-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[102];N-(pyridin-3-ylmethyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[103];N-((6-(4-methylpiperazin-1-yl)pyridin-3-yl)methyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[104];N-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)methyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[105];N-(1-methylpiperidin-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline-4-carboxamide[106];(5-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-morpholinopiperidin-1-yl)methanone[107]; and(6-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-yl)(4,7-diazaspiro[2.5]octan-7-yl)methanone[108]; or a pharmaceutically acceptable salt thereof.
 21. The compoundaccording to claim 10, wherein the compound of Formula Ib is selectedfrom the group consisting of:5-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole [109];2-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine [110];7-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[111]; 6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[112];N-(2,2-difluoroethyl)-6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[113];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[114];4-fluoro-1-isopropyl-6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-benzo[d]imidazole[115];4-fluoro-6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[116];1-isopropyl-6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-imidazo[4,5-b]pyridine[117];1-isopropyl-6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-imidazo[4,5-c]pyridine[118];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[119];7-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[120];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[121];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[122];4-methoxy-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[123];4-methoxy-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[124];4-methoxy-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[125];N-(2,2-difluoroethyl)-5-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[126];(R)-5-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[127];5-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[128];5-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[129];(5-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[130];(5-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[131];(5-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[132];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[134];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[135]; 5-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[136];5-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[137];6′-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[138]; 3-(chroman-6-yl)-4-methoxy-1H-pyrrolo[2,3-b]pyridine [139];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[140];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[141];7-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[142];8-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[143]; 6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [144];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [145];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [146];4-methoxy-6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [147];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[148];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[149];6-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[150];2-methyl-5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[151];2-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[152];7-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[153];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[154];N-(2,2-difluoroethyl)-6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[155];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[156];4-fluoro-1-isopropyl-2-methyl-6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[157];4-fluoro-2-methyl-6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[158];1-isopropyl-2-methyl-6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[159];1-isopropyl-2-methyl-6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[160];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[161];7-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[162];1-methyl-6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[163];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[164];4-(1-methyl-1H-pyrazol-4-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[165];4-(1-methyl-1H-pyrazol-4-yl)-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[166];4-(1-methyl-1H-pyrazol-4-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[167];N-(2,2-difluoroethyl)-5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[168];(R)-5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[169];5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[170];5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[171];(5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[172];(5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[173];(5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[174];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[176];1′-methyl-6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[177];5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[178];3,3-dimethyl-5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[179];6′-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[180];3-(chroman-6-yl)-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine[181];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[182];4,4-dimethyl-6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[183];7-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[184];8-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[1,4]oxazepin-5(2H)-one[185];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[186];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[187];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[188];4-methoxy-6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[189];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[190];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[191];6-(4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[192]; 5-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[1411]; 2-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1412];7-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1413]; 6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1414];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide[1415];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1416];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole[1417];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1418];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine[1419];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridine[1420];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1421];7-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1422];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[1423];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1424];6-chloro-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1425];6-chloro-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1426];6-chloro-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1427];5-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)pyrazolo[1,5-a]pyridine-3-carboxamide[1428];(R)-5-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1429];5-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1430];5-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1431];(5-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1432];(5-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1433];(5-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1434];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1436];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1437]; 5-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1438];5-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1439];6′-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1440]; 6-chloro-3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridine [1441];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1442];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1443];7-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1444];8-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1445]; 6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [1446];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [1447];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [1448];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methoxyquinazoline [1449];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1450];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1451];6-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1452]; 2-methyl-5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[1453]; 2-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1454];7-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1455]; 6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1456];N-(2,2-difluoroethyl)-6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1457];6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1458];4-fluoro-1-isopropyl-2-methyl-6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1459];4-fluoro-2-methyl-6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1460];1-isopropyl-2-methyl-6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[1461];1-isopropyl-2-methyl-6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[1462];6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1463];7-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1464];1-methyl-6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[1465];6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1466];6-methyl-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1467];6-methyl-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1468];6-methyl-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1469];N-(2,2-difluoroethyl)-5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1470];(R)-5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1471];5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1472];5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1473];(5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1474];(5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1475];(5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1476];6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1478];1′-methyl-6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1479]; 5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1480];3,3-dimethyl-5-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1481];6′-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1482]; 3-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine [1483];6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1484];4,4-dimethyl-6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1485];7-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1486];8-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1487]; 6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [1488];6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [1489];6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [1490];4-methoxy-6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [1491];6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1492];6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1493];6-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1494];5-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[1495];2-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1496];7-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1497];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1498];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide[1499];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1500];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole[1501];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1502];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine[1503];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridine[1504];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1505];7-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1506];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[1507];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1508];6-cyclopropyl-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1509];6-cyclopropyl-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1510];6-cyclopropyl-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1511];5-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)pyrazolo[1,5-a]pyridine-3-carboxamide[1512];(R)-5-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1513];5-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1514];5-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1515];(5-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1516];(5-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1517];(5-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1518];6-cyclopropyl-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1519];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1520];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1521];5-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1523];6′-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1524]; 3-(chroman-6-yl)-6-cyclopropyl-1H-pyrrolo[2,3-b]pyridine [1525];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1526];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1527];7-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1528];8-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1529]; 6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [1530];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [1531];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [1532];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methoxyquinazoline[1533];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1534];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1535];6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1536];5-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[1537];2-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1538];7-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1539];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1540];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide[1541];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1542];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole[1543];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1544];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine[1545];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridine[1546];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1547];7-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1548];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[1549];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1550];6-cyclobutyl-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1551];6-cyclobutyl-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1552];6-cyclobutyl-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1553];5-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)pyrazolo[1,5-a]pyridine-3-carboxamide[1554];(R)-5-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1555];5-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1556];5-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1557];(5-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1558];(5-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1559];(5-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1560];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1562];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1563]; 5-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1564];5-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1565];6′-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1566]; 3-(chroman-6-yl)-6-cyclobutyl-1H-pyrrolo[2,3-b]pyridine [1567];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1568];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1569];7-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1570];8-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1571]; 6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [1572];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [1573];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [1574];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methoxyquinazoline[1575];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1576];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1577];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1578];5-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[1579];2-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1580];7-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1581];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1582];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide[1583];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1584];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole[1585];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1586];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine[1587];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridine[1588];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1589];7-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1590];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[1591];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1592];6-cyclopentyl-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1593];6-cyclopentyl-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1594];6-cyclopentyl-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1595];5-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)pyrazolo[1,5-a]pyridine-3-carboxamide[1596];(R)-5-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1597];5-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1598];5-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1599];(5-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1600];(5-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1601];(5-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1602];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1604];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1605]; 5-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1606];5-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1607];6′-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1608]; 3-(chroman-6-yl)-6-cyclopentyl-1H-pyrrolo[2,3-b]pyridine [1609];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1610];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1611];7-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1612];8-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1613]; 6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [1614];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [1615];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [1616];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methoxyquinazoline[1617];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1618];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1619];6-(6-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1620];5-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[1621];2-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1622];7-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1623];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1624];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide[1625];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1626];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole[1627];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1628];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine[1629];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridine[1630];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1631];7-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1632];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[1633];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1634];6-(cyclobutylmethyl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1635];6-(cyclobutylmethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1636];6-(cyclobutylmethyl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1637];5-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)pyrazolo[1,5-a]pyridine-3-carboxamide[1638];(R)-5-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1639];5-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1640];5-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1641];(5-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1642];(5-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1643];(5-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1644];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1646];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1647];5-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1648];5-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1649];6′-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1650]; 3-(chroman-6-yl)-6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridine[1651];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1652];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1653];7-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1654];8-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1655]; 6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1656];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1657];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1658];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methoxyquinazoline[1659];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1660];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1661];6-(6-(cyclobutylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1662]; 5-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[1663]; 2-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1664];7-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1665];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1666];N-(2,2-difluoroethyl)-6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1667];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1668];4-fluoro-1-isopropyl-6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-benzo[d]imidazole[1669];4-fluoro-6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1670];1-isopropyl-6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-imidazo[4,5-b]pyridine[1671];1-isopropyl-6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-imidazo[4,5-c]pyridine[1672];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1673];7-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1674];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[1675];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1676];6-methoxy-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1677];6-methoxy-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1678];6-methoxy-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1679];N-(2,2-difluoroethyl)-5-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1680];(R)-5-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1681];5-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1682];5-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1683];(5-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1684];(5-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1685];(5-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1686];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1688];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1689]; 5-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1690];5-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1691];6′-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1692]; 3-(chroman-6-yl)-6-methoxy-1H-pyrrolo[2,3-b]pyridine [1693];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1694];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1695];7-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1696];8-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1697]; 6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [1698];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [1699];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [1700];4-methoxy-6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [1701];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1702];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1703];6-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1704];5-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[1705];2-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1706];7-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1707];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1708];N-(2,2-difluoroethyl)-6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1709];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1710];4-fluoro-1-isopropyl-6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-benzo[d]imidazole[1711];4-fluoro-6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1712];1-isopropyl-6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-imidazo[4,5-b]pyridine[1713];1-isopropyl-6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-imidazo[4,5-c]pyridine[1714];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1715];7-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1716];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[1717];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1718];6-(difluoromethoxy)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1719];6-(difluoromethoxy)-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1720];6-(difluoromethoxy)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1721];N-(2,2-difluoroethyl)-5-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1722];(R)-5-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1723];5-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1724];5-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1725];(5-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1726];(5-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1727];(5-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1728];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1730];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1731];5-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1732];5-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1733];6′-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1734]; 3-(chroman-6-yl)-6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridine[1735];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1736];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1737];7-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1738];8-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1739]; 6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1740]; 6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1741]; 6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1742];4-methoxy-6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1743];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1744];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1745];6-(6-(difluoromethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1746]; 5-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[1747]; 2-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1748];7-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1749]; 6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1750];N-(2,2-difluoroethyl)-6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1751];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1752];4-fluoro-1-isopropyl-6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-benzo[d]imidazole[1753];4-fluoro-6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1754];1-isopropyl-6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-imidazo[4,5-b]pyridine[1755];1-isopropyl-6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-imidazo[4,5-c]pyridine[1756];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1757];7-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1758];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[1759];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1760];6-ethoxy-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1761];6-ethoxy-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1762];6-ethoxy-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1763];N-(2,2-difluoroethyl)-5-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1764];(R)-5-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1765];5-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1766];5-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1767];(5-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1768];(5-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1769];(5-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1770];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1772];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1773]; 5-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1774];5-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1775];6′-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1776]; 3-(chroman-6-yl)-6-ethoxy-1H-pyrrolo[2,3-b]pyridine [1777];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1778];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1779];7-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1780];8-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1781]; 6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [1782];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [1783];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [1784];4-methoxy-6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [1785];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1786];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1787];6-(6-ethoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1788];(3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1789];(3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1790];7-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1791];(3-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1792];N-(2,2-difluoroethyl)-6-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1793];(3-(imidazo[1,2-a]pyrimidin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1794];(3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1795];(3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1796];(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1797];(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1798];(3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1799];(3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1800];(3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1801];(3-(imidazo[1,2-b]pyridazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1802];(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1803];(3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1804];(3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1805];N-(2,2-difluoroethyl)-5-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1806];(R)-5-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1807];5-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1808];5-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1809];(5-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1810];(5-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1811];(5-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1812];6-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1814];6-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1815];5-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1816];5-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1817];6′-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1818]; (3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol [1819];6-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1820];6-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1821];7-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1822];8-(6-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1823]; (3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1824]; (3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1825]; (3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1826];(3-(4-methoxyquinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1827];(3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1828];(3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1829];(3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)methanol[1830];1-methyl-N-(3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1831];1-methyl-N-(3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1832];1-methyl-N-(3-(1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1833];N-(3-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1834];N-(2,2-difluoroethyl)-6-(6-(1-methylpiperidine-4-carboxamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1835];N-(3-(imidazo[1,2-a]pyrimidin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1836];N-(3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1837];N-(3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1838];N-(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1839];N-(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1840];N-(3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1841];N-(3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1842];1-methyl-N-(3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1843];N-(3-(imidazo[1,2-b]pyridazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1844];1-methyl-N-(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1845];1-methyl-N-(3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1846];1-methyl-N-(3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1847];N-(2,2-difluoroethyl)-5-(6-(1-methylpiperidine-4-carboxamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1848];(R)-5-(6-(1-methylpiperidine-4-carboxamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1849];N-(1-methylpiperidin-4-yl)-5-(6-(1-methylpiperidine-4-carboxamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1850];5-(6-(1-methylpiperidine-4-carboxamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1851];1-methyl-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1852];1-methyl-N-(3-(3-(4-methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1853];1-methyl-N-(3-(3-(morpholine-4-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1854];1-methyl-N-(3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1856];1-methyl-N-(3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1857];1-methyl-N-(3-(1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1858];N-(3-(3,3-dimethyl-1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1859];1-methyl-N-(3-(3′-oxospiro[cyclohexane-1,1′-isoindolin]-6′-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1860];N-(3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1861];1-methyl-N-(3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1862];N-(3-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1863];1-methyl-N-(3-(4-oxospiro[chromane-2,4′-piperidin]-7-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1864];1-methyl-N-(3-(5-oxo-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-8-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1865];1-methyl-N-(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1866];1-methyl-N-(3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1867];1-methyl-N-(3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1868];N-(3-(4-methoxyquinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)-1-methylpiperidine-4-carboxamide[1869];1-methyl-N-(3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1870];1-methyl-N-(3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1871];1-methyl-N-(3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)piperidine-4-carboxamide[1872];N-(3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1873];N-(3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1874];N-(3-(1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1875];N-(3-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1876];N-(2,2-difluoroethyl)-6-(6-(isonicotinamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1877];N-(3-(imidazo[1,2-a]pyrimidin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1878];N-(3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1879];N-(3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1880];N-(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1881];N-(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1882];N-(3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1883];N-(3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1884]; N-(3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide [1885];N-(3-(imidazo[1,2-b]pyridazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1886];N-(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1887];N-(3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1888];N-(3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1889];N-(2,2-difluoroethyl)-5-(6-(isonicotinamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1890];(R)-5-(6-(isonicotinamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1891];5-(6-(isonicotinamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1892];5-(6-(isonicotinamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1893];N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1894];N-(3-(3-(4-methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1895];N-(3-(3-(morpholine-4-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1896];N-(3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1898];N-(3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1899];N-(3-(1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1900];N-(3-(3,3-dimethyl-1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1901];N-(3-(3′-oxospiro[cyclohexane-1,1′-isoindolin]-6′-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1902];N-(3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1903];N-(3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1904];N-(3-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1905];N-(3-(4-oxospiro[chromane-2,4′-piperidin]-7-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1906];N-(3-(5-oxo-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-8-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1907];N-(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1908];N-(3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1909];N-(3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1910];N-(3-(4-methoxyquinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1911];N-(3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1912];N-(3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1913];N-(3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)isonicotinamide[1914];3-(2-methyl-2H-indazol-5-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1915];N-(3-(4-methylpiperazin-1-yl)phenyl)-3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1916];7-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1917];3-(imidazo[1,2-a]pyridin-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1918];N-(2,2-difluoroethyl)-6-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1919];3-(imidazo[1,2-a]pyrimidin-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1920];3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1921];3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1922];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1923];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1924];3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1925];3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1926];3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1927];3-(imidazo[1,2-b]pyridazin-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1928];N-(3-(4-methylpiperazin-1-yl)phenyl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1929];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1930];N-(3-(4-methylpiperazin-1-yl)phenyl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1931];N-(2,2-difluoroethyl)-5-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1932];(R)-5-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1933];5-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1934];5-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1935];(5-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1936];(4-methylpiperazin-1-yl)(5-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1937];(5-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1938];6-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1940];1′-methyl-6-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1941];5-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1942];3,3-dimethyl-5-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1943];6′-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1944];3-(chroman-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1945];6-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1946];4,4-dimethyl-6-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1947];7-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1948];8-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[1,4]oxazepin-5(2H)-one[1949];N-(3-(4-methylpiperazin-1-yl)phenyl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1950];N-(3-(4-methylpiperazin-1-yl)phenyl)-3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1951];N-(3-(4-methylpiperazin-1-yl)phenyl)-3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1952];3-(4-methoxyquinazolin-6-yl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1953];N-(3-(4-methylpiperazin-1-yl)phenyl)-3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1954];N-(3-(4-methylpiperazin-1-yl)phenyl)-3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine[1955];6-(6-((3-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1956];2-methyl-5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[1957];2-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1958];7-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1959];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1960];N-(2,2-difluoroethyl)-6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1961];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1962];4-fluoro-1-isopropyl-2-methyl-6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1963];4-fluoro-2-methyl-6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1964];1-isopropyl-2-methyl-6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[1965];1-isopropyl-2-methyl-6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[1966];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1967];7-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1968];1-methyl-6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[1969];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1970];6-(1-methyl-1H-pyrazol-4-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1971];6-(1-methyl-1H-pyrazol-4-yl)-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1972];6-(1-methyl-1H-pyrazol-4-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1973];N-(2,2-difluoroethyl)-5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1974];(R)-5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1975];5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1976];5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1977];(5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1978];(5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1979];(5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1980];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1982];1′-methyl-6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1983];5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1984];3,3-dimethyl-5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1985];6′-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1986];3-(chroman-6-yl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine[1987];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1988];4,4-dimethyl-6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1989];7-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1990];8-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[1,4]oxazepin-5(2H)-one[1991];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1992];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1993];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1994];4-methoxy-6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1995];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1996];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1997];6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1998]; 2-methyl-5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[1999]; 2-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[2000];7-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[2001]; 6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[2002];N-(2,2-difluoroethyl)-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[2003];6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[2004];4-fluoro-1-isopropyl-2-methyl-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[2005];4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[2006];1-isopropyl-2-methyl-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[2007];1-isopropyl-2-methyl-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[2008];6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[2009];7-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[2010];1-methyl-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[2011];6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[2012];6-phenyl-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[2013];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-6-phenyl-1H-pyrrolo[2,3-b]pyridine[2014];6-phenyl-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[2015];N-(2,2-difluoroethyl)-5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[2016];(R)-5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[2017];N-(1-methylpiperidin-4-yl)-5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[2018];5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[2019];(5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[2020];(4-methylpiperazin-1-yl)(5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[2021];morpholino(5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[2022];6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[2024];1′-methyl-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[2025]; 5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[2026];3,3-dimethyl-5-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[2027];6′-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[2028]; 3-(chroman-6-yl)-6-phenyl-1H-pyrrolo[2,3-b]pyridine [2029];6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[2030];4,4-dimethyl-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[2031];7-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[2032];8-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[2033]; 6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [2034];6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [2035];6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [2036];4-methoxy-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [2037];4-(4-methylpiperazin-1-yl)-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[2038];4-((1-methylpiperidin-4-yl)oxy)-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[2039];N-(1-methylpiperidin-4-yl)-6-(6-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[2040];6-(6-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrazine[2042];4-fluoro-1-isopropyl-6-(6-isopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-1H-benzo[d]imidazole[2045];3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-6-carboxamide[2048];N-((6-(4-methylpiperazin-1-yl)pyridin-3-yl)methyl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine[2051];N-((6-(1H-imidazol-1-yl)pyridin-3-yl)methyl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine[2052];6-(6-(cyclopropylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[2053];N-(pyridin-4-yl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-6-carboxamide[2054]; 5-(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-6-yl)thiazole[2055]; and6-(6-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)-N-methylimidazo[1,2-a]pyridine-3-carboxamide[2056]; or a pharmaceutically acceptable salt thereof.
 22. The compoundaccording to claim 15, wherein the compound of Formula Ie is selectedfrom the group consisting of:5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole [193];2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine [194];7-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[195]; 6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[196];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide[197];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[198];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole[199];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[200];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine[201];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridine[202];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[203];7-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[204];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[205];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[206];5-chloro-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[207];5-chloro-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[208];5-chloro-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[209];5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)pyrazolo[1,5-a]pyridine-3-carboxamide[210];(R)-5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[211];5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[212];5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[213];(5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[214];(5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[215];(5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[216];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[218];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[219];5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[221];6′-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[222]; 5-chloro-3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridine [223];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[225];7-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[226];8-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[227]; 6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [229];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [230];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methoxyquinazoline [231];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[232];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[233];6-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[234]; 5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[235]; 2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[236];7-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[237]; 6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[238];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide[239];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[240];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole[241];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[242];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine[243];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridine[244];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[245];7-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[246];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[247];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[248];5-fluoro-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[249];5-fluoro-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[250];5-fluoro-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[251];5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)pyrazolo[1,5-a]pyridine-3-carboxamide[252];(R)-5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[253];5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[254];5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[255];(5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[256];(5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[257];(5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[258];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[260];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[261];5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[263];6′-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[264]; 5-fluoro-3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridine [265];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[267];7-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[268];8-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[269]; 6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [271];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [272];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methoxyquinazoline [273];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[274];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[275];6-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[276]; 2-methyl-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[277]; 2-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[278];7-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[279]; 6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[280];N-(2,2-difluoroethyl)-6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[281];6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[282];4-fluoro-1-isopropyl-2-methyl-6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[283];4-fluoro-2-methyl-6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[284];1-isopropyl-2-methyl-6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[285];1-isopropyl-2-methyl-6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[286];6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[287];7-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[288];1-methyl-6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[289];6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[290];5-methyl-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[291];5-methyl-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[292];5-methyl-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[293];N-(2,2-difluoroethyl)-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[294];(R)-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[295];5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[296];5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[297];(5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[298];(5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[299];(5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[300];6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[302];1′-methyl-6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[303]; 5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one [304];3,3-dimethyl-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[305];6′-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[306]; 3-(chroman-6-yl)-5-methyl-1H-pyrrolo[2,3-b]pyridine [307];6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[308];4,4-dimethyl-6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[309];7-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[310];8-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[311]; 6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [313];6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [314];4-methoxy-6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [315];6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[316];6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[317];6-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[318];2-methyl-5-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[319];2-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[320];7-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[321];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[322];N-(2,2-difluoroethyl)-6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[323];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[324];4-fluoro-1-isopropyl-2-methyl-6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[325];4-fluoro-2-methyl-6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[326];1-isopropyl-2-methyl-6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[327];1-isopropyl-2-methyl-6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[328];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[329];7-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[330];1-methyl-6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[331];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[332];5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[333];5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[334];5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[335];N-(2,2-difluoroethyl)-5-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[336];(R)-5-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[337];5-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[338];5-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[339];(5-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[340];(5-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[341];(5-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[342];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[344];1′-methyl-6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[345];5-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[346];3,3-dimethyl-5-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[347];6′-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[348];3-(chroman-6-yl)-5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[349];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[350];4,4-dimethyl-6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[351];7-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[352];8-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[353];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[354];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[355];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[356];4-methoxy-6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[357];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[358];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[359];6-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[360];2-methyl-5-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[361];2-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[362];7-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[363];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[364];N-(2,2-difluoroethyl)-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[365];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[366];4-fluoro-1-isopropyl-2-methyl-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[367];4-fluoro-2-methyl-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[368];1-isopropyl-2-methyl-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[369];1-isopropyl-2-methyl-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[370];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[371];7-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[372];1-methyl-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[373];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[374];5-(4-methylpiperazin-1-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[375];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-1)]pyridine[376];5-(4-methylpiperazin-1-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[377];N-(2,2-difluoroethyl)-5-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[378];(R)-5-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[379];5-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[380];5-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[381];(5-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[382];(4-methylpiperazin-1-yl)(5-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[383];(5-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[384];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[386];1′-methyl-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[387];5-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[388];3,3-dimethyl-5-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[389];6′-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[390];3-(chroman-6-yl)-5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine[391];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[392];4,4-dimethyl-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[393];7-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[394];8-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[395];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[396];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[397];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[398];4-methoxy-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[399];4-(4-methylpiperazin-1-yl)-6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[400];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[401];6-(5-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[402];2-methyl-5-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[403];2-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[404];7-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[405];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[406];N-(2,2-difluoroethyl)-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[407];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[408];4-fluoro-1-isopropyl-2-methyl-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[409];4-fluoro-2-methyl-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[410];1-isopropyl-2-methyl-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[411];1-isopropyl-2-methyl-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[412];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[413];7-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[414];1-methyl-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[415];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[416];5-((4-methylpiperazin-1-yl)methyl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-1)]pyridine[417];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-1)]pyridine[418];5-((4-methylpiperazin-1-yl)methyl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-1)]pyridine[419];N-(2,2-difluoroethyl)-5-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[420];(R)-5-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[421];5-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[422];5-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[423];(5-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[424];(4-methylpiperazin-1-yl)(5-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[425];(5-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[426];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[428];1′-methyl-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[429];5-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[430];3,3-dimethyl-5-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[431];6′-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[432];3-(chroman-6-yl)-5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridine[433];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[434];4,4-dimethyl-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[435];7-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[436];8-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[437];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[438];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[439];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[440];4-methoxy-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[441];4-(4-methylpiperazin-1-yl)-6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[442];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[443];6-(5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[444];3-(2-methyl-2H-indazol-5-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[445];N-(1-methylpiperidin-4-yl)-3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[446];N-(1-methylpiperidin-4-yl)-3-(1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[447];3-(imidazo[1,2-a]pyridin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[448];N-(2,2-difluoroethyl)-6-(5-((1-methylpiperidin-4-yl)carbamoyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[449];3-(imidazo[1,2-a]pyrimidin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[450];3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[451];3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[452];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[453];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[454];3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[455];3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[456];3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[457];3-(imidazo[1,2-b]pyridazin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[458];N-(1-methylpiperidin-4-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[459];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[460];N-(1-methylpiperidin-4-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[461];3-(3-((2,2-difluoroethyl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[462];(R)-N-(1-methylpiperidin-4-yl)-3-(3-((1,1,1-trifluoropropan-2-yl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[463];N-(1-methylpiperidin-4-yl)-3-(3-((1-methylpiperidin-4-yl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[464];N-(1-methylpiperidin-4-yl)-3-(3-(pyridin-3-ylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[465];N-(1-methylpiperidin-4-yl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[466];3-(3-(4-methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[467];N-(1-methylpiperidin-4-yl)-3-(3-(morpholine-4-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[468];N-(1-methylpiperidin-4-yl)-3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[470];3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[471];N-(1-methylpiperidin-4-yl)-3-(1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[472];3-(3,3-dimethyl-1-oxoisoindolin-5-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[473];N-(1-methylpiperidin-4-yl)-3-(3′-oxospiro[cyclohexane-1,1′-isoindolin]-6′-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[474];3-(chroman-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[475];N-(1-methylpiperidin-4-yl)-3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[476];3-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[477];N-(1-methylpiperidin-4-yl)-3-(4-oxospiro[chromane-2,4′-piperidin]-7-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[478];N-(1-methylpiperidin-4-yl)-3-(5-oxo-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-8-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[479];N-(1-methylpiperidin-4-yl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[480];N-(1-methylpiperidin-4-yl)-3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[481];N-(1-methylpiperidin-4-yl)-3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[482];3-(4-methoxyquinazolin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[483];3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[484];N-(1-methylpiperidin-4-yl)-3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[485];N-(1-methylpiperidin-4-yl)-3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[486];(3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[487];(4-methylpiperazin-1-yl)(3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[488];7-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[489];(3-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[490];N-(2,2-difluoroethyl)-6-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[491];(3-(imidazo[1,2-a]pyrimidin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[492];(3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[493];(3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[494];(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[495];(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[496];(3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[497];(3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[498];(3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[499];(3-(imidazo[1,2-b]pyridazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[500];(4-methylpiperazin-1-yl)(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[501];(3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[502];(4-methylpiperazin-1-yl)(3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[503];N-(2,2-difluoroethyl)-5-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[504];(R)-5-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[505];5-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[506];5-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[507];(4-methylpiperazin-1-yl)(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[508];(4-methylpiperazin-1-yl)(5-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[509];(4-methylpiperazin-1-yl)(3-(3-(morpholine-4-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[510];6-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[512];1′-methyl-6-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[513];5-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[514];3,3-dimethyl-5-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[515];6′-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[516];(3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[517];6-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[518];4,4-dimethyl-6-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[519];7-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[520];8-(5-(4-methylpiperazine-1-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[521];(4-methylpiperazin-1-yl)(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[522];(4-methylpiperazin-1-yl)(3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[523];(4-methylpiperazin-1-yl)(3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[524];(3-(4-methoxyquinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-methylpiperazin-1-yl)methanone[525];(4-methylpiperazin-1-yl)(3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[526];(4-methylpiperazin-1-yl)(3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[527];(4-methylpiperazin-1-yl)(3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[528];(3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[529];(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)(3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[530];7-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[531];(3-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[532];N-(2,2-difluoroethyl)-6-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[533];(3-(imidazo[1,2-a]pyrimidin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[534];(3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[535];(3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[536];(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[537];(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[538];(3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[539];(3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[540];(3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[541];(3-(imidazo[1,2-b]pyridazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[542];(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[543];(3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[544];(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)(3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[545];N-(2,2-difluoroethyl)-5-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[546];5-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-((R)-1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[547];5-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[548];5-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[549];(5-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[550];(5-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[551];(5-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[552];6-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[554];1′-methyl-6-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[555];5-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[556];3,3-dimethyl-5-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[557];6′-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[558];(3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[559];6-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[560];4,4-dimethyl-6-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[561];7-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[562];8-(5-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[563];(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[564];(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)(3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[565];(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)(3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[566];(3-(4-methoxyquinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone[567];(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)(3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[568];(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)(3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[569];(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)(3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[570];(3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[571];(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)(3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[572];7-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[573];(3-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[574];(3-(3-(((2,2-difluoroethyl)amino)methyl)imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[575];(3-(imidazo[1,2-a]pyrimidin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[576];(3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[577];(3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[578];(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[579];(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[580];(3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[581];(3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[582];(3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[583];(3-(imidazo[1,2-b]pyridazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[584];(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[585];(3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[586];(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)(3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[587];N-(2,2-difluoroethyl)-5-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[588];(R)-5-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[589];5-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[590];5-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[591];(5-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[592];(5-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[593];(5-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[594];6-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[596];1′-methyl-6-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[597];5-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[598];3,3-dimethyl-5-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[599];6′-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[600];(3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[601];6-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[602];4,4-dimethyl-6-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[603];7-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[604];8-(5-(2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-7-carbonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[605];(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[606];(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)(3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[607];(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)(3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[608];(3-(4-methoxyquinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methanone[609];(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)(3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[610];(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)(3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[611];(2-methyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)(3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[612];1-methyl-N-(3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[613];1-methyl-N-(3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[614];1-methyl-N-(3-(1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[615];N-(3-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[616];N-(2,2-difluoroethyl)-6-(5-(1-methylpiperidine-4-carboxamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[617];N-(3-(imidazo[1,2-a]pyrimidin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[618];N-(3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[619];N-(3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[620];N-(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[621];N-(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[622];N-(3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[623];N-(3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[624];1-methyl-N-(3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[625];N-(3-(imidazo[1,2-b]pyridazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[626];1-methyl-N-(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[627];1-methyl-N-(3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[628];1-methyl-N-(3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[629];N-(2,2-difluoroethyl)-5-(5-(1-methylpiperidine-4-carboxamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[630];(R)-5-(5-(1-methylpiperidine-4-carboxamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[631];N-(1-methylpiperidin-4-yl)-5-(5-(1-methylpiperidine-4-carboxamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[632];5-(5-(1-methylpiperidine-4-carboxamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[633];1-methyl-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[634];1-methyl-N-(3-(3-(4-methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[635];1-methyl-N-(3-(3-(morpholine-4-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[636];1-methyl-N-(3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[638];1-methyl-N-(3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[639];1-methyl-N-(3-(1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[640];N-(3-(3,3-dimethyl-1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[641];1-methyl-N-(3-(3′-oxospiro[cyclohexane-1,1′-isoindolin]-6′-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[642];N-(3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[643];1-methyl-N-(3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[644];N-(3-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[645];1-methyl-N-(3-(4-oxospiro[chromane-2,4′-piperidin]-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[646];1-methyl-N-(3-(5-oxo-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-8-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[647];1-methyl-N-(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[648];1-methyl-N-(3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[649];1-methyl-N-(3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[650];N-(3-(4-methoxyquinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-methylpiperidine-4-carboxamide[651];1-methyl-N-(3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[652];1-methyl-N-(3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[653];1-methyl-N-(3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)piperidine-4-carboxamide[654];3-(2-methyl-2H-indazol-5-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[655];N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[656];3-(1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[657];3-(imidazo[1,2-a]pyridin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[658];N-(2,2-difluoroethyl)-6-(5-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)carbamoyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[659];3-(imidazo[1,2-a]pyrimidin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[660];3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[661];3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[662];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[663];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[664];3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[665];3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[666];3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[667];3-(imidazo[1,2-b]pyridazin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[668];N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[669];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[670];N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[671];3-(3-((2,2-difluoroethyl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[672];(R)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-((1,1,1-trifluoropropan-2-yl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[673];3-(3-((1-methylpiperidin-4-yl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[674];N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-(pyridin-3-ylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[675];N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[676];3-(3-(4-methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[677];3-(3-(morpholine-4-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[678];3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[680];3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[681];3-(1-oxoisoindolin-5-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[682];3-(3,3-dimethyl-1-oxoisoindolin-5-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[683];3-(3′-oxospiro[cyclohexane-1,1′-isoindolin]-6′-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[684];3-(chroman-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[685];3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[686];3-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[687];3-(4-oxospiro[chromane-2,4′-piperidin]-7-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[688];3-(5-oxo-2,3,4,5-tetrahydrobenzo[1,4]oxazepin-8-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[689];N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[690];N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[691];N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[692];3-(4-methoxyquinazolin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[693];3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[694];3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[695];3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-N-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[696];3-(2-methyl-2H-indazol-5-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[697];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[698];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[699];3-(imidazo[1,2-a]pyridin-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[700];N-(2,2-difluoroethyl)-6-(5-((1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)carbamoyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[701];3-(imidazo[1,2-a]pyrimidin-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[702];3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[703];3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[704];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[705];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[706];3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[707];3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[708];3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[709];3-(imidazo[1,2-b]pyridazin-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[710];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[711];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[712];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[713];3-(3-((2,2-difluoroethyl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[714];(R)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-((1,1,1-trifluoropropan-2-yl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[715];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-((1-methylpiperidin-4-yl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[716];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-(pyridin-3-ylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[717];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[718];3-(3-(4-methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[719];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-(morpholine-4-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[720];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[722];3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[723];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[724];3-(3,3-dimethyl-1-oxoisoindolin-5-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[725];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(3′-oxospiro[cyclohexane-1,1′-isoindolin]-6′-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[726];3-(chroman-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[727];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[728];3-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[729];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(4-oxospiro[chromane-2,4′-piperidin]-7-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[730];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(5-oxo-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-8-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[731];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[732];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[733];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[734];3-(4-methoxyquinazolin-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[735];3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[736];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[737];N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[738];N-(5-fluoropyridin-3-yl)-3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[739];N-(5-fluoropyridin-3-yl)-3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[740];N-(5-fluoropyridin-3-yl)-3-(1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[741];N-(5-fluoropyridin-3-yl)-3-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[742];N-(2,2-difluoroethyl)-6-(5-((5-fluoropyridin-3-yl)carbamoyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[743];N-(5-fluoropyridin-3-yl)-3-(imidazo[1,2-a]pyrimidin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[744];3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(5-fluoropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[745];3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-N-(5-fluoropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[746];N-(5-fluoropyridin-3-yl)-3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[747];N-(5-fluoropyridin-3-yl)-3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[748];3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(5-fluoropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[749];3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(5-fluoropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[750];N-(5-fluoropyridin-3-yl)-3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[751];N-(5-fluoropyridin-3-yl)-3-(imidazo[1,2-b]pyridazin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[752];N-(5-fluoropyridin-3-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[753];N-(5-fluoropyridin-3-yl)-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[754];N-(5-fluoropyridin-3-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[755];3-(3-((2,2-difluoroethyl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-N-(5-fluoropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[756];(R)-N-(5-fluoropyridin-3-yl)-3-(3-((1,1,1-trifluoropropan-2-yl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[757];N-(5-fluoropyridin-3-yl)-3-(3-((1-methylpiperidin-4-yl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[758];N-(5-fluoropyridin-3-yl)-3-(3-(pyridin-3-ylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[759];N-(5-fluoropyridin-3-yl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[760];N-(5-fluoropyridin-3-yl)-3-(3-(4-methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[761];N-(5-fluoropyridin-3-yl)-3-(3-(morpholine-4-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[762];N-(5-fluoropyridin-3-yl)-3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[764];N-(5-fluoropyridin-3-yl)-3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[765];N-(5-fluoropyridin-3-yl)-3-(1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[766];3-(3,3-dimethyl-1-oxoisoindolin-5-yl)-N-(5-fluoropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[767];N-(5-fluoropyridin-3-yl)-3-(3′-oxospiro[cyclohexane-1,1′-isoindolin]-6′-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[768];3-(chroman-6-yl)-N-(5-fluoropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[769];N-(5-fluoropyridin-3-yl)-3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[770];3-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-N-(5-fluoropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[771];N-(5-fluoropyridin-3-yl)-3-(4-oxospiro[chromane-2,4′-piperidin]-7-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[772];N-(5-fluoropyridin-3-yl)-3-(5-oxo-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-8-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[773];N-(5-fluoropyridin-3-yl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[774];N-(5-fluoropyridin-3-yl)-3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[775];N-(5-fluoropyridin-3-yl)-3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[776];N-(5-fluoropyridin-3-yl)-3-(4-methoxyquinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[777];N-(5-fluoropyridin-3-yl)-3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[778];N-(5-fluoropyridin-3-yl)-3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[779];N-(5-fluoropyridin-3-yl)-3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[780];3-(2-methyl-2H-indazol-5-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[781];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[782];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[783];3-(imidazo[1,2-a]pyridin-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[784];N-(2,2-difluoroethyl)-6-(5-((6-(4-methylpiperazin-1-yl)pyridin-3-yl)carbamoyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[785];3-(imidazo[1,2-a]pyrimidin-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[786];3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[787];3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[788];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[789];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[790];3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[791];3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[792];3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[793];3-(imidazo[1,2-b]pyridazin-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[794];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[795];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[796];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[797];3-(3-((2,2-difluoroethyl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[798];(R)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(3-((1,1,1-trifluoropropan-2-yl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[799];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(3-((1-methylpiperidin-4-yl)carbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[800];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(3-(pyridin-3-ylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[801];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[802];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(3-(4-methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[803];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(3-(morpholine-4-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[804];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[806];3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[807];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[808];3-(3,3-dimethyl-1-oxoisoindolin-5-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[809];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(3′-oxospiro[cyclohexane-1,1′-isoindolin]-6′-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[810];3-(chroman-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[811];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[812];3-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[813];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(4-oxospiro[chromane-2,4′-piperidin]-7-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[814];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(5-oxo-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-8-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[815];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[816];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[817];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[818];3-(4-methoxyquinazolin-6-yl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[819];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[820];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[821];N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide[822];N-(3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[823];2-(piperazin-1-yl)-N-(3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)isonicotinamide[824];N-(3-(1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[825];N-(3-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[826];N-(2,2-difluoroethyl)-6-(5-(2-(piperazin-1-yl)isonicotinamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[827];N-(3-(imidazo[1,2-a]pyrimidin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[828];N-(3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[829];N-(3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[830];N-(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-1)]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[831];N-(3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[832];N-(3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[833];N-(3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[834]; N-(3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[835];N-(3-(imidazo[1,2-b]pyridazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[836];2-(piperazin-1-yl)-N-(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)isonicotinamide[837];N-(3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[838];2-(piperazin-1-yl)-N-(3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)isonicotinamide[839];N-(2,2-difluoroethyl)-5-(5-(2-(piperazin-1-yl)isonicotinamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[840];(R)-5-(5-(2-(piperazin-1-yl)isonicotinamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[841];N-(1-methylpiperidin-4-yl)-5-(5-(2-(piperazin-1-yl)isonicotinamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[842];5-(5-(2-(piperazin-1-yl)isonicotinamido)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[843];2-(piperazin-1-yl)-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)isonicotinamide[844];N-(3-(3-(4-methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[845];N-(3-(3-(morpholine-4-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[846];N-(3-(3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[848];N-(3-(1′-methyl-3-oxo-2,3-dihydrospiro[indene-1,4′-piperidin]-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[849];N-(3-(1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[850];N-(3-(3,3-dimethyl-1-oxoisoindolin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[851];N-(3-(3′-oxospiro[cyclohexane-1,1′-isoindolin]-6′-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[852];N-(3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[853];N-(3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[854];N-(3-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[855];N-(3-(4-oxospiro[chromane-2,4′-piperidin]-7-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[856];N-(3-(5-oxo-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-8-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[857];2-(piperazin-1-yl)-N-(3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)isonicotinamide[858];2-(piperazin-1-yl)-N-(3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)isonicotinamide[859];2-(piperazin-1-yl)-N-(3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)isonicotinamide[860];N-(3-(4-methoxyquinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[861];N-(3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[862];N-(3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[863];N-(3-(4-((1-methylpiperidin-4-yl)amino)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)isonicotinamide[864];3-(2-methyl-2H-indazol-5-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[865];N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[866];7-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[867];3-(imidazo[1,2-a]pyridin-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[868];N-(2,2-difluoroethyl)-6-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[869];3-(imidazo[1,2-a]pyrimidin-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[870];3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[871];3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[872];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[873];3-(1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[874];3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[875];3-([1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[876];3-(1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[877];3-(imidazo[1,2-b]pyridazin-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[878];N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[879];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[880];N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[881];N-(2,2-difluoroethyl)-5-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[882];(R)-5-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[883];5-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[884];5-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[885];(5-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[886];(4-methylpiperazin-1-yl)(5-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[887];(5-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[888];6-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[890];1′-methyl-6-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[891];5-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[892];3,3-dimethyl-5-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[893];6′-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[894];3-(chroman-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[895];6-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[896];4,4-dimethyl-6-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[897];7-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[898];8-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[899];N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-3-(quinolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[900];N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-3-(quinoxalin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[901];N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-3-(quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[902];3-(4-methoxyquinazolin-6-yl)-N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[903];N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-3-(4-(4-methylpiperazin-1-yl)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[904];N-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-3-(4-((1-methylpiperidin-4-yl)oxy)quinazolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine[905];6-(5-((2-(4-methylpiperazin-1-yl)pyridin-4-yl)amino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[906]; 2-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[908];7-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[909]; 6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[910];N-(2,2-difluoroethyl)-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[911];6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[912];4-fluoro-1-isopropyl-2-methyl-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[913];4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[914];1-isopropyl-2-methyl-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[915];1-isopropyl-2-methyl-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[916];6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[917];7-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[918];1-methyl-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[919];6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[920];5-phenyl-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[921];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridine[922];5-phenyl-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[923];N-(2,2-difluoroethyl)-5-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[924];(R)-5-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[925];N-(1-methylpiperidin-4-yl)-5-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[926];5-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[927];(5-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[928];(4-methylpiperazin-1-yl)(5-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[929];morpholino(5-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[930];6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[932];1′-methyl-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[933]; 5-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one [934];3,3-dimethyl-5-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[935];6′-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[936]; 3-(chroman-6-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridine [937];6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[938];4,4-dimethyl-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[939];7-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[940];8-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[941]; 6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [942];6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [943];6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [944];4-methoxy-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [945];4-(4-methylpiperazin-1-yl)-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[946];4-((1-methylpiperidin-4-yl)oxy)-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[947];N-(1-methylpiperidin-4-yl)-6-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[948];2-methyl-5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[949];2-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[950];7-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[951];6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[952];N-(2,2-difluoroethyl)-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[953];6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[954];4-fluoro-1-isopropyl-2-methyl-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[955];4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[956];1-isopropyl-2-methyl-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[957];1-isopropyl-2-methyl-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[958];6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[959];7-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[960];1-methyl-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[961];6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[962];3-(pyrazoN-(2,2-difluoroethyl)-5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamidelo[1,5-a]pyridin-5-yl)-5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridine [963];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridine[964];3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridine[965];N-(2,2-difluoroethyl)-5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[966];(R)-5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[967];N-(1-methylpiperidin-4-yl)-5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[968];N-(pyridin-3-yl)-5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[969];piperidin-1-yl(5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[970];(4-methylpiperazin-1-yl)(5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[971]; morpholino(5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[972];6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[974];1′-methyl-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[975]; 5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[976];3,3-dimethyl-5-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[977];6′-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[978]; 3-(chroman-6-yl)-5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridine [979];6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[980];4,4-dimethyl-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[981];7-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[982];8-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[983]; 6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline [984];6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline [985];6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline [986];4-methoxy-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[987];4-(4-methylpiperazin-1-yl)-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[988];4-((1-methylpiperidin-4-yl)oxy)-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[989];N-(1-methylpiperidin-4-yl)-6-(5-(o-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[990];5-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[991];2-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[992];7-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[993];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[994];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide[995];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[996];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole[997];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[998];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine[999];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridine[1000];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1001];7-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1002];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[1003];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1004];5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1005];5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1006];5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1007];5-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2,2-difluoroethyl)pyrazolo[1,5-a]pyridine-3-carboxamide[1008];(R)-5-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1009];5-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1010];5-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1011];(5-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1012];(5-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1013];(5-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1014];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1016];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1017];5-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1018];5-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1019];6′-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1020];3-(chroman-6-yl)-5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine[1021];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1022];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1023];7-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1024];8-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1025];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1026];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1027];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1028];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methoxyquinazoline[1029];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1030];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1031];6-(5-(3,4-difluoro-5-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1032];2-methyl-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[1033];2-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1034];7-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1035];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1036];N-(2,2-difluoroethyl)-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1037];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1038];4-fluoro-1-isopropyl-2-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1039];4-fluoro-2-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1040];1-isopropyl-2-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[1041];1-isopropyl-2-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[1042];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1043];7-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1044];1-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[1045];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1046];5-(1-methyl-1H-pyrazol-4-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-1)]pyridine[1047];5-(1-methyl-1H-pyrazol-4-yl)-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1048];5-(1-methyl-1H-pyrazol-4-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1049];N-(2,2-difluoroethyl)-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1050];(R)-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1051];5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1052];5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1053];(5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-1)]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1054];(5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-1)]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1055];(5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-1)]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1056];5-(1-methyl-1H-pyrazol-4-yl)-3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1057];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1058];1′-methyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1059];3,3-dimethyl-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1061];6′-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-1)]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1062];3-(chroman-6-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-1)]pyridine[1063];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1064];4,4-dimethyl-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1065];7-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1066];8-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1067];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1068];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1069];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1070];4-methoxy-6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1071];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1072];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1073];6-(5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1074];2-methyl-5-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[1075];2-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1076];7-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1077];6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1078];N-(2,2-difluoroethyl)-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1079];6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1080];4-fluoro-1-isopropyl-2-methyl-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1081];4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1082];1-isopropyl-2-methyl-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-1)]pyridine[1083];1-isopropyl-2-methyl-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[1084];6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1085];7-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1086];1-methyl-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[1087];6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1088];3-(pyrazolo[1,5-a]pyridin-5-yl)-5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-1)]pyridine[1089];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-1)]pyridine[1090];3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine[1091];N-(2,2-difluoroethyl)-5-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1092];(R)-N-(1,1,1-trifluoropropan-2-yl)-5-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1093];N-(1-methylpiperidin-4-yl)-5-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1094];N-(pyridin-3-yl)-5-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1095];piperidin-1-yl(5-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1096];(4-methylpiperazin-1-yl)(5-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1097];morpholino(5-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1098];6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1100];1′-methyl-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1101];5-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1102];3,3-dimethyl-5-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1103];6′-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1104];3-(chroman-6-yl)-5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine[1105];6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1106];4,4-dimethyl-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1107];7-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1108];8-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1109];6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1110];6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1111];6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1112];4-methoxy-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1113];4-(4-methylpiperazin-1-yl)-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1114];4-((1-methylpiperidin-4-yl)oxy)-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1115];N-(1-methylpiperidin-4-yl)-6-(5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[1116];5-methyl-3-(3-(2-methyl-2H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine[1117];2-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1118];7-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1119];3-(3-(imidazo[1,2-a]pyridin-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine[1120];N-(2,2-difluoroethyl)-6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1121];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1122];3-(3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine[1123];3-(3-(4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine[1124];1-isopropyl-2-methyl-6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[1125];1-isopropyl-2-methyl-6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[1126];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1127];7-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1128];1-methyl-6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[1129];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1130];5-methyl-3-(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine[1131];5-methyl-3-(3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine[1132];5-methyl-3-(3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine[1133];N-(2,2-difluoroethyl)-5-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1134];(R)-5-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1135];5-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1136];5-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1137];(5-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1138];(5-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1139];(5-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1140];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1142];1′-methyl-6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1143];5-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1144];3,3-dimethyl-5-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1145];6′-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1146];3-(3-(chroman-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine[1147];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1148];4,4-dimethyl-6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1149];7-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1150];8-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1151];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1152];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1153];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1154];4-methoxy-6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1155];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1156];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1157];6-(5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1158];2-methyl-5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[1159];2-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1160];7-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1161];6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1162];N-(2,2-difluoroethyl)-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1163];6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1164];4-fluoro-1-isopropyl-2-methyl-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1165];4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1166];1-isopropyl-2-methyl-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[1167];1-isopropyl-2-methyl-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[1168];6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1169];7-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1170];1-methyl-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[1171];6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1172];3-(pyrazolo[1,5-a]pyridin-5-yl)-5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1173];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1174];5-(pyridin-3-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1175];N-(2,2-difluoroethyl)-5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1176];(R)-5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1177];N-(1-methylpiperidin-4-yl)-5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1178];N-(pyridin-3-yl)-5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1179];piperidin-1-yl(5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1180];(4-methylpiperazin-1-yl)(5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1181];morpholino(5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1182];6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1184];1′-methyl-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1185];5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1186];3,3-dimethyl-5-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1187];6′-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1188]; 3-(chroman-6-yl)-5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1189];6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1190];4,4-dimethyl-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1191];7-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1192];8-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1193]; 6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1194]; 6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1195]; 6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1196];4-methoxy-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1197];4-(4-methylpiperazin-1-yl)-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1198];4-((1-methylpiperidin-4-yl)oxy)-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1199];N-(1-methylpiperidin-4-yl)-6-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[1200];2-methyl-5-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[1201];2-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1202];7-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1203];6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1204];N-(2,2-difluoroethyl)-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1205];6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1206];4-fluoro-1-isopropyl-2-methyl-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1207];4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1208];1-isopropyl-2-methyl-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[1209];1-isopropyl-2-methyl-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[1210];6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1211];7-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1212];1-methyl-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[1213];6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1214];5-(2-methylpyridin-3-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1215];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1216];5-(2-methylpyridin-3-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1217];N-(2,2-difluoroethyl)-5-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1218];(R)-5-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1219];N-(1-methylpiperidin-4-yl)-5-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1220];5-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1221];(5-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1222];(4-methylpiperazin-1-yl)(5-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1223];(5-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1224];6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1226];1′-methyl-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1227];5-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1228];3,3-dimethyl-5-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1229];6′-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1230];3-(chroman-6-yl)-5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1231];6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1232];4,4-dimethyl-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1233];7-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1234];8-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1235];6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1236];6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1237];6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1238];4-methoxy-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1239];4-(4-methylpiperazin-1-yl)-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1240];4-((1-methylpiperidin-4-yl)oxy)-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1241];N-(1-methylpiperidin-4-yl)-6-(5-(2-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[1242];2-methyl-5-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[1243];2-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1244];7-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1245];6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1246];N-(2,2-difluoroethyl)-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1247];6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1248];4-fluoro-1-isopropyl-2-methyl-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1249];4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1250];1-isopropyl-2-methyl-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[1251];1-isopropyl-2-methyl-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[1252];6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1253];7-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1254];1-methyl-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[1255];6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1256];5-(4-methylpyridin-3-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1257];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1258];5-(4-methylpyridin-3-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1259];N-(2,2-difluoroethyl)-5-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1260];(R)-5-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1261];N-(1-methylpiperidin-4-yl)-5-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1262];5-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1263];(5-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1264];(4-methylpiperazin-1-yl)(5-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1265];(5-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1266];6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1268];1′-methyl-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1269];5-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1270];3,3-dimethyl-5-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1271];6′-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1272];3-(chroman-6-yl)-5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1273];6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1274];4,4-dimethyl-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1275];7-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1276];8-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one[1277];6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1278];6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1279];6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1280];4-methoxy-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1281];4-(4-methylpiperazin-1-yl)-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1282];4-((1-methylpiperidin-4-yl)oxy)-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1283];N-(1-methylpiperidin-4-yl)-6-(5-(4-methylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazolin-4-amine[1284];5-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-2H-indazole[1285];2-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1286];7-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1287];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1288];N-(2,2-difluoroethyl)-6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1289];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1290];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole[1291];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-fluoro-2-methyl-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1292];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-b]pyridine[1293];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-isopropyl-2-methyl-1H-imidazo[4,5-c]pyridine[1294];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1295];7-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1296];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1H-benzo[d][1,2,3]triazole[1297];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1298];5-(2,4-dimethylpyridin-3-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1299];5-(2,4-dimethylpyridin-3-yl)-3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1300];5-(2,4-dimethylpyridin-3-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1301];N-(2,2-difluoroethyl)-5-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1302];(R)-5-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1303];5-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1304];5-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1305];(5-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1306];(5-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[1307];(5-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1308];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1310];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1′-methylspiro[indene-1,4′-piperidin]-3(2H)-one[1311];5-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1312];5-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,3-dimethylisoindolin-1-one[1313];6′-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1314];3-(chroman-6-yl)-5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1315];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1316];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one[1317];7-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1318];8-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[1,4]oxazepin-5(2H)-one[1319];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1320];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1321];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1322];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methoxyquinazoline[1323];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(4-methylpiperazin-1-yl)quinazoline[1324];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1325];6-(5-(2,4-dimethylpyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1326];2-methyl-5-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[1327];2-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1328];7-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1329];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1330];N-(2,2-difluoroethyl)-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1331];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1332];4-fluoro-1-isopropyl-2-methyl-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1333];4-fluoro-2-methyl-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1334];1-isopropyl-2-methyl-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[1335];1-isopropyl-2-methyl-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[1336];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1337];7-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1338];1-methyl-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[1339];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1340];5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1341];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1342];5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-1)]pyridine[1343];N-(2,2-difluoroethyl)-5-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1344];(R)-5-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1345];5-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1346];5-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1347];(5-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1348];(4-methylpiperazin-1-yl)(5-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1349];(5-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1350];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1352];1′-methyl-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1353];5-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1354];3,3-dimethyl-5-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1355];6′-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1356];3-(chroman-6-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine[1357];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1358];4,4-dimethyl-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1359];7-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1360];8-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[1,4]oxazepin-5(2H)-one[1361];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1362];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1363];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1364];4-methoxy-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1365];4-(4-methylpiperazin-1-yl)-6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1366];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1367];6-(5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1368];2-methyl-5-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2H-indazole[1369];2-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)thieno[2,3-c]pyridine[1370];7-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one[1371];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine[1372];N-(2,2-difluoroethyl)-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide[1373];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-a]pyrimidine[1374];4-fluoro-1-isopropyl-2-methyl-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d]imidazole[1375];4-fluoro-2-methyl-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole[1376];1-isopropyl-2-methyl-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-b]pyridine[1377];1-isopropyl-2-methyl-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-imidazo[4,5-c]pyridine[1378];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1379];7-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine[1380];1-methyl-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-benzo[d][1,2,3]triazole[1381];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)imidazo[1,2-b]pyridazine[1382];5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1383];3-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-5-yl)-5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1384];5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-3-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine[1385];N-(2,2-difluoroethyl)-5-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1386];(R)-5-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1,1,1-trifluoropropan-2-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1387];5-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1388];5-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carboxamide[1389];(5-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone[1390];(4-methylpiperazin-1-yl)(5-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[1391];(5-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(morpholino)methanone[1392];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1394];1′-methyl-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[indene-1,4′-piperidin]-3(2H)-one[1395];5-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1396];3,3-dimethyl-5-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)isoindolin-1-one[1397];6′-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one[1398];3-(chroman-6-yl)-5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine[1399];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1400];4,4-dimethyl-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one[1401];7-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)spiro[chromane-2,4′-piperidin]-4-one[1402];8-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydrobenzo[1,4]oxazepin-5(2H)-one[1403];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoline[1404];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxaline[1405];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1406];4-methoxy-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1407];4-(4-methylpiperazin-1-yl)-6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinazoline[1408];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-((1-methylpiperidin-4-yl)oxy)quinazoline[1409];6-(5-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine[1410];(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)(3-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[2041];3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylicacid [2043];(3-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)methanone[2044];3-(3-(4-methylpiperazine-1-carbonyl)pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile[2046];(5-(5-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(4-methylpiperazin-1-yl)methanone[2047];(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)(3-(pyrazolo[1,5-a]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone[2049]; and(4-methylpiperazin-1-yl)(5-(5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone[2050]; or a pharmaceutically acceptable salt thereof.
 23. Apharmaceutical composition comprising a therapeutically effective amountof a compound of claim 1, or a pharmaceutically acceptable salt thereof,and a pharmaceutically acceptable excipient.
 24. A pharmaceuticalcomposition comprising a therapeutically effective amount of a compoundof claim 7, or a pharmaceutically acceptable salt thereof, and apharmaceutically acceptable excipient.
 25. A pharmaceutical compositioncomprising a therapeutically effective amount of a compound of claim 10,or a pharmaceutically acceptable salt thereof, and a pharmaceuticallyacceptable excipient.
 26. A pharmaceutical composition comprising atherapeutically effective amount of a compound of claim 15, or apharmaceutically acceptable salt thereof, and a pharmaceuticallyacceptable excipient.
 27. A method of treating a disorder or disease ina patient, wherein the disorder or disease is selected from the groupconsisting of: a neurological disorder, diabetes, and cancer, the methodcomprising administering to the patient a therapeutically effectiveamount of a compound of claim 1, or a pharmaceutically acceptable salt,or a pharmaceutical composition of claim
 23. 28. A method of treating adisorder or disease in a patient, wherein the disorder or disease isselected from the group consisting of: a neurological disorder,diabetes, and cancer, the method comprising administering to the patienta therapeutically effective amount of a compound of claim 7, or apharmaceutically acceptable salt, or a pharmaceutical composition ofclaim
 24. 29. A method of treating a disorder or disease in a patient,wherein the disorder or disease is selected from the group consistingof: a neurological disorder, diabetes, and cancer, the method comprisingadministering to the patient a therapeutically effective amount of acompound of claim 10, or a pharmaceutically acceptable salt, or apharmaceutical composition of claim
 25. 30. A method of treating adisorder or disease in a patient, wherein the disorder or disease isselected from the group consisting of: a neurological disorder,diabetes, and cancer, the method comprising administering to the patienta therapeutically effective amount of a compound of claim 15, or apharmaceutically acceptable salt, or a pharmaceutical composition ofclaim 26.